Ammonium Hydroxide → Citalopram

HRID 2230923

반응식

HRID 2230923 반응식
[C:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[C:9]([C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)([CH2:13][CH2:14][CH2:15][N:16]([CH3:18])[CH3:17])[O:8][CH2:7]2)(O)=O.S(N)([NH2:29])(=O)=O.S(Cl)(Cl)=O.[OH-].[NH4+]>S1(CCCC1)(=O)=O.CCCCCCC.O>[C:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[C:9]([C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)([CH2:13][CH2:14][CH2:15][N:16]([CH3:17])[CH3:18])[O:8][CH2:7]2)#[N:29]

참가 물질

8

반응물 4

HCID 14923Ammonium HydroxideHCID 24386Thionyl ChlorideHCID 82267SulfamideHCID 99280441-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydro-5-Isobenzofurancarboxylic acid

생성물 1

HCID 2771Citalopram

시약·촉매·용매 3

HCID 962Water용매HCID 8900Heptane용매2회HCID 31347Sulfolane용매

반응 조건

온도
130 °C

실험 절차

5-Carboxy-1-(4-fluorophenyl)-1-(3-dimethylaminopropyl)-1,3-dihydro-isobenzofuran (5 g, 0.015 mole) and sulfamide (1.65 g, 0.017 mole) were dissolved in sulfolane (15 mL). Thionylchloride (2.25 g, 0.019 mole) was added at room temperature and the temperature of the reaction mixture was raised to 130° C. for 2 hours. The reaction mixture was allowed to cool to 75° C. and water (25 mL) was added. The temperature was held at 75° C. for 15 min, and then the reaction mixture was cooled to room temperature. pH was ajusted to 9 with ammonium hydroxide and then n-heptane (75 mL) was added. The temperature was raised to 70° C. and the hot n-heptane layer was isolated from which the title compound crystallised on cooling. Yield 3.77 g. Purity (HPLC peak area)>97%.

후처리

  1. temperatureto cool to 75° C.
  2. temperaturethe reaction mixture was cooled to room temperature
  3. temperatureThe temperature was raised to 70° C.

출처 및 근거

ORD 기록
ord-88300376b7be48dc9e3b2271621cbed7
출처 데이터셋
uspto-grants-2002_07
특허 번호
US06426422B1

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