Sodium Hydroxide → Citalopram

To a stirred solution of 5-aminomethyl-1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran (0.5 g, 1.5 mmol) in dichloromethane (10 mL) was added an aqueous solution of potassium bisulfate and sodium hydroxide (19 mL; 0.2 M in K2S2O8, 3.8 mmol; 0.4 M in NaOH, 7.6 mmol), followed by an aqueous solution of nickel sulfate (1.5 mL, 40 mM, 61 μmol). The mixture was stirred vigorously for 4 days, and was then filtered through celite. The filtrate was partitioned between aqueous sulfuric acid (2 M) and toluene. The aqueous layer was separated, and the pH of the mixture was adjusted to >9 by the addition of aqueous ammonia solution (25% w/v). The solution was extracted with toluene, and this latter toluene extract was dried over magnesium sulfate and evaporated to give the free base of citalopram as a very pale yellow oil (0.35 g, 70%).

1. filtrationwas then filtered through celite
2. customThe filtrate was partitioned between aqueous sulfuric acid (2 M) and toluene
3. customThe aqueous layer was separated
4. additionthe pH of the mixture was adjusted to >9 by the addition of aqueous ammonia solution (25% w/v)
5. extractionThe solution was extracted with toluene
6. extractionthis latter toluene extract
7. dry with materialwas dried over magnesium sulfate
8. customevaporated

ORDレコード

ord-a18f67ca611c4f07a46a38ae2cef77dd

出典データセット

uspto-grants-2003_12

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06660873B2