Ammonium Hydroxide → Citalopram

HRID 2230923

反応式

HRID 2230923 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

HCID 2771Citalopram

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8900Heptane溶媒2 回HCID 31347Sulfolane溶媒

反応条件

温度
130 °C

実験手順

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%.

後処理

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

出典と根拠

ORDレコード
ord-88300376b7be48dc9e3b2271621cbed7
出典データセット
uspto-grants-2002_07
特許番号
US06426422B1

関連ノート

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