Water → 2-{2-[2-(4-(3-Fluorophenyl)piperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carboxamide

HRID 1789351ノート

反応式

HRID 1789351 の反応式
[N-:1]=[C:2]=[O:3].[K+].O.[F:6][C:7]1[CH:8]=[C:9]([N:13]2[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[CH:28]3[NH:32][CH2:31][CH2:30][S:29]3)[CH2:15][CH2:14]2)[CH:10]=[CH:11][CH:12]=1.C(=O)(O)[O-].[Na+]>C(O)C.C(O)(=O)C>[F:6][C:7]1[CH:8]=[C:9]([N:13]2[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[CH:28]3[N:32]([C:2]([NH2:1])=[O:3])[CH2:31][CH2:30][S:29]3)[CH2:15][CH2:14]2)[CH:10]=[CH:11][CH:12]=1

参加物

7

反応物 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 11051572Potassio isocyanate2 回HCID 13768101HCID 13768101、化合物

生成物 1

HCID 137680352-{2-[2-(4-(3-Fluorophenyl)piperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carboxamide収率 87.3%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒2 回HCID 702Ethanol溶媒

実験手順

A mixture of 1.12 g of potassium isocyanate, 10 ml of water and 2 ml of acetic acid is added to a solution of 2.68 g of 2-{2-[2-(4-(3-fluorophenyl)piperazin-1-yl)ethyloxy]phenyl}thiazolidine in 20 ml of ethanol, and the mixture is stirred at room temperature for 2 hours. A mixture of 0.56 g of potassium isocyanate and 0.5 ml of acetic acid is added to said mixture, and the mixture is stirred at the same temperature for 2 hours. The mixture is made alkaline with sodium bicarbonate and concentrated under reduced pressure to remove solvent. The residue is extracted with ethyl acetate. The extract is washed with a saturated sodium chloride solution, dried and then concentrated under reduced pressure to remove solvent. The residue is purified by silica gel chromatograph (solvent, ethyl acetate), and the resultant product is recrystallized from a mixture of ethyl acetate and ether. 2.6 g of 2-{2-[2-(4-(3-fluorophenyl)piperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carboxamide are obtained.

後処理

  1. additionis added
  2. stirringthe mixture is stirred at the same temperature for 2 hours
  3. concentrationconcentrated under reduced pressure
  4. customto remove solvent
  5. extractionThe residue is extracted with ethyl acetate
  6. washThe extract is washed with a saturated sodium chloride solution
  7. customdried
  8. concentrationconcentrated under reduced pressure
  9. customto remove solvent
  10. customThe residue is purified by silica gel chromatograph (solvent, ethyl acetate)
  11. customthe resultant product is recrystallized from a mixture of ethyl acetate and ether

出典と根拠

ORDレコード
ord-999349dc79214221aaf430c3096dbad1
出典データセット
uspto-grants-1987_08
特許番号
US04689327

反応ノート

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