{"id":826,"date":"2011-01-24T16:45:00","date_gmt":"2011-01-24T16:45:00","guid":{"rendered":"https:\/\/psiconautica.org\/wordpress\/?p=826"},"modified":"2022-01-31T11:19:57","modified_gmt":"2022-01-31T11:19:57","slug":"synthesis-of-7-bromotryptamine-hcl","status":"publish","type":"post","link":"https:\/\/psiconautica.org\/wordpress\/quimica-avanzada\/synthesis-of-7-bromotryptamine-hcl\/","title":{"rendered":"Synthesis of 7-bromotryptamine HCl"},"content":{"rendered":"<hr \/>\n<p>Synthesis of 7-bromotryptamine HCl<\/p>\n<p>To a stirred suspension of 2-bromophenylhydrazine hydrochloride (25.8 g, 115 mmol) in chloroform (500 mL) was added saturated sodium carbonate solution (500 mL). The mixture was stirred for 30 minutes and extracted with chloroform (2&#215;200 mL). The combined organic phases were concentrated to afford the hydrazine free base as a yellow oil. This oil was dissolved in methanol (100 mL) and treated slowly with 4-chlorobutanal (12.3 g, 115 mmol). The mixture was placed in a sealable tube and purged with nitrogen for 10 minutes. The tube was sealed and placed in an oil bath preheated to 95\u00b0C. Heating was continued for 18 hours. The resulting dark solution was cooled to ambient temperature and concentrated under reduced pressure. The residue was partitioned between chloroform\/methanol (75\/25 by volume) and aqueous sodium carbonate solution. The organic phase was concentrated and the crude tryptamine was purified by flash chromatography on silica gel (0-25% methanol gradient in chloroform as eluent). Fractions containing product were combined and concentrated. The oil was dissolved in diethyl ether (300 mL) containing 1% methanol and treated with dry HCl gas. The hydrochloride salt was isolated by filtration, washed with 2-propanol (50 mL) and diethyl ether (100 mL) and dried to afford 7-bromotryptamine hydrochloride (3.6 g) as a pale solid.<\/p>\n<h4>References<\/h4>\n<p><b>[1]<\/b> US Pat 5508284<\/p>\n<hr \/>\n","protected":false},"excerpt":{"rendered":"<p>Synthesis of 7-bromotryptamine HCl To a stirred suspension of 2-bromophenylhydrazine hydrochloride (25.8 g, 115 mmol) in chloroform (500 mL) was added saturated sodium carbonate solution (500 mL). The mixture was stirred for 30 minutes and extracted with chloroform (2&#215;200 mL). The combined organic phases were concentrated to afford the hydrazine free base as a yellow [&hellip;]<\/p>\n","protected":false},"author":1,"featured_media":1615,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[24],"tags":[],"class_list":["post-826","post","type-post","status-publish","format-standard","has-post-thumbnail","category-quimica-avanzada"],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.8 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Synthesis of 7-bromotryptamine HCl - Psicon\u00e1utica<\/title>\n<meta name=\"robots\" content=\"noindex, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<meta property=\"og:locale\" content=\"es_ES\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Synthesis of 7-bromotryptamine HCl - Psicon\u00e1utica\" \/>\n<meta property=\"og:description\" content=\"Synthesis of 7-bromotryptamine HCl To a stirred suspension of 2-bromophenylhydrazine hydrochloride (25.8 g, 115 mmol) in chloroform (500 mL) was added saturated sodium carbonate solution (500 mL). The mixture was stirred for 30 minutes and extracted with chloroform (2&#215;200 mL). The combined organic phases were concentrated to afford the hydrazine free base as a yellow [&hellip;]\" \/>\n<meta property=\"og:url\" content=\"https:\/\/psiconautica.org\/wordpress\/quimica-avanzada\/synthesis-of-7-bromotryptamine-hcl\/\" \/>\n<meta property=\"og:site_name\" content=\"Psicon\u00e1utica\" \/>\n<meta property=\"article:published_time\" content=\"2011-01-24T16:45:00+00:00\" \/>\n<meta property=\"article:modified_time\" content=\"2022-01-31T11:19:57+00:00\" \/>\n<meta property=\"og:image\" content=\"https:\/\/psiconautica.org\/wordpress\/wp-content\/uploads\/2011\/01\/1614x1000-1.jpg\" \/>\n\t<meta property=\"og:image:width\" content=\"1200\" \/>\n\t<meta property=\"og:image:height\" content=\"800\" \/>\n\t<meta property=\"og:image:type\" content=\"image\/jpeg\" \/>\n<meta name=\"author\" content=\"Ra\u00fal del Pino\" \/>\n<meta name=\"twitter:card\" content=\"summary_large_image\" \/>\n<meta name=\"twitter:label1\" content=\"Escrito por\" \/>\n\t<meta name=\"twitter:data1\" content=\"Ra\u00fal del Pino\" \/>\n\t<meta name=\"twitter:label2\" content=\"Tiempo de lectura\" \/>\n\t<meta name=\"twitter:data2\" content=\"1 minuto\" \/>\n<script type=\"application\/ld+json\" class=\"yoast-schema-graph\">{\"@context\":\"https:\\\/\\\/schema.org\",\"@graph\":[{\"@type\":\"Article\",\"@id\":\"https:\\\/\\\/psiconautica.org\\\/wordpress\\\/quimica-avanzada\\\/synthesis-of-7-bromotryptamine-hcl\\\/#article\",\"isPartOf\":{\"@id\":\"https:\\\/\\\/psiconautica.org\\\/wordpress\\\/quimica-avanzada\\\/synthesis-of-7-bromotryptamine-hcl\\\/\"},\"author\":{\"name\":\"Ra\u00fal del Pino\",\"@id\":\"https:\\\/\\\/psiconautica.org\\\/wordpress\\\/#\\\/schema\\\/person\\\/3afbb90b66878c42e9d66e8e261f3d29\"},\"headline\":\"Synthesis of 7-bromotryptamine HCl\",\"datePublished\":\"2011-01-24T16:45:00+00:00\",\"dateModified\":\"2022-01-31T11:19:57+00:00\",\"mainEntityOfPage\":{\"@id\":\"https:\\\/\\\/psiconautica.org\\\/wordpress\\\/quimica-avanzada\\\/synthesis-of-7-bromotryptamine-hcl\\\/\"},\"wordCount\":205,\"commentCount\":0,\"image\":{\"@id\":\"https:\\\/\\\/psiconautica.org\\\/wordpress\\\/quimica-avanzada\\\/synthesis-of-7-bromotryptamine-hcl\\\/#primaryimage\"},\"thumbnailUrl\":\"https:\\\/\\\/psiconautica.org\\\/wordpress\\\/wp-content\\\/uploads\\\/2011\\\/01\\\/1614x1000-1.jpg\",\"articleSection\":[\"Qu\u00edmica avanzada\"],\"inLanguage\":\"es\",\"potentialAction\":[{\"@type\":\"CommentAction\",\"name\":\"Comment\",\"target\":[\"https:\\\/\\\/psiconautica.org\\\/wordpress\\\/quimica-avanzada\\\/synthesis-of-7-bromotryptamine-hcl\\\/#respond\"]}]},{\"@type\":\"WebPage\",\"@id\":\"https:\\\/\\\/psiconautica.org\\\/wordpress\\\/quimica-avanzada\\\/synthesis-of-7-bromotryptamine-hcl\\\/\",\"url\":\"https:\\\/\\\/psiconautica.org\\\/wordpress\\\/quimica-avanzada\\\/synthesis-of-7-bromotryptamine-hcl\\\/\",\"name\":\"Synthesis of 7-bromotryptamine HCl - 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