Hydrochloric Acid → Tiagabine

HRID 619241ノート

反応式

HRID 619241 の反応式
CC[O:3][C:4]([C@H:6]1[CH2:11][N:10]([CH2:12][CH2:13][CH:14]=[C:15]([C:22]2[S:26][CH:25]=[CH:24][C:23]=2[CH3:27])[C:16]2[S:20][CH:19]=[CH:18][C:17]=2[CH3:21])[CH2:9][CH2:8][CH2:7]1)=[O:5].Cl>O>[CH3:27][C:23]1[CH:24]=[CH:25][S:26][C:22]=1[C:15]([C:16]1[S:20][CH:19]=[CH:18][C:17]=1[CH3:21])=[CH:14][CH2:13][CH2:12][N:10]1[CH2:11][C@H:6]([C:4]([OH:5])=[O:3])[CH2:7][CH2:8][CH2:9]1

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 11555813PIP017

生成物 1

HCID 60648Tiagabine収率 87.1%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
57.5 °C

実験手順

To a 1 L flask, 50 g of tiagabine ethyl ester, 750 ml of water and 11 g of conc. hydrochloric acid were charged. The mixture was heated to reflux for 2 hours and then ethanol/water, a total of 400 ml, was distilled off over a period of 4 hours. The remaining solution was stirred under reflux overnight. It was cooled to 55-60° C. and then an additional 37.5 g of conc. hydrochloric acid was added over a period of 5 min. The solution was cooled to 50-52° C. and was stirred at this temperature for 18 hours. The resulting precipitate was collected by filtration and was washed with 20 ml of water. The product was dried under vacuum at room temperature to give 40.5 g of Tiagabine, hydrochloride.

後処理

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 hours
  3. distillationethanol/water, a total of 400 ml, was distilled off over a period of 4 hours
  4. temperatureunder reflux overnight
  5. additionan additional 37.5 g of conc. hydrochloric acid was added over a period of 5 min
  6. temperatureThe solution was cooled to 50-52° C.
  7. stirringwas stirred at this temperature for 18 hours
  8. filtrationThe resulting precipitate was collected by filtration
  9. washwas washed with 20 ml of water
  10. customThe product was dried under vacuum at room temperature

出典と根拠

ORDレコード
ord-9ab4f5ca5ae6452fb3d6404f2a9ea59e
出典データセット
uspto-grants-1999_09
特許番号
US05958951

反応ノート

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