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

HRID 1789351노트

반응식

HRID 1789351 반응식
[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

참가 물질

7

반응물 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 11051572Potassio isocyanate2회HCID 13768101HCID 13768101, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 176Acetic Acid용매2회HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-999349dc79214221aaf430c3096dbad1
출처 데이터셋
uspto-grants-1987_08
특허 번호
US04689327

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