Ammonium Hydroxide → Citalopram

HRID 2230923

Reaktionsgleichung

[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]

Komponenten

Reaktionsbedingungen

Temperatur: 130 °C

Versuchsvorschrift

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%.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag: ord-88300376b7be48dc9e3b2271621cbed7
Quelldatensatz: uspto-grants-2002_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06426422B1

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