Sodium Hydroxide → Citalopram

HRID 432047

반응식

HRID 432047 반응식
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH2:19][CH2:20][CH2:21][N:22]([CH3:24])[CH3:23])([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)[O:7][CH2:6]2.S(=O)(=O)(O)[O-].[K+].[OH-].[Na+]>ClCCl.S([O-])([O-])(=O)=O.[Ni+2]>[CH3:23][N:22]([CH2:21][CH2:20][CH2:19][C:8]1([C:12]2[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=2)[O:7][CH2:6][C:5]2[CH:4]=[C:3]([C:2]#[N:1])[CH:11]=[CH:10][C:9]1=2)[CH3:24]

참가 물질

6

반응물 3

HCID 14798Sodium HydroxideHCID 516920Potassium bisulfateHCID 114729275-Aminomethyl-1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran

생성물 1

HCID 2771Citalopram

시약·촉매·용매 2

HCID 24586Nickel Sulfate촉매HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-a18f67ca611c4f07a46a38ae2cef77dd
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06660873B2

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