Triethylamine → 4-(3-Indolyl)-1-[(4-oxo-3-thiazolidinyl)acetyl]piperidine

HRID 34910

반응식

HRID 34910 반응식
[O:1]=[C:2]1[CH2:6][S:5][CH2:4][N:3]1[CH2:7][C:8](Cl)=[O:9].[NH:11]1[CH2:16][CH2:15][CH:14]([C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[NH:19][CH:18]=2)[CH2:13][CH2:12]1.C(N(CC)CC)C>O1CCCC1.C(Cl)(Cl)Cl>[NH:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:17]([CH:14]2[CH2:15][CH2:16][N:11]([C:8](=[O:9])[CH2:7][N:3]3[C:2](=[O:1])[CH2:6][S:5][CH2:4]3)[CH2:12][CH2:13]2)=[CH:18]1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 7022353-(4-Piperidinyl)-1H-indoleHCID 212972254-Oxo-3-thiazolidinylacetyl chloride

생성물 1

HCID 212972224-(3-Indolyl)-1-[(4-oxo-3-thiazolidinyl)acetyl]piperidine수율 27.5%

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of 4-oxo-3-thiazolidinylacetyl chloride (1.75 g) in tetrahydrofuran (5.00 ml) was added dropsise to a suspension of 3-(4-piperidyl)indole (2.00 g) and triethylamine (4.10 ml) in a mixture of tetrahydrofuran (15.0 ml) and chloroform (5.00 ml) at 4° to 7° C. with stirring. After the mixture was allowed to stir for 1 hour with ice-bath cooling, the resultant precipitate was removed by filtration and the solvent was evaporated in vacuo. The residue was mixed with saturated aqueous sodium hydrogen carbonate (10.0 ml) and the mixture was extracted with chloroform (20.0 ml). The extract was washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was recrystallized from a mixture of methanol and acetone to give 4-(3-indolyl)-1-[(4-oxo-3-thiazolidinyl)acetyl]piperidine (0.92 g) as slightly brown prisms.

후처리

  1. stirringto stir for 1 hour with ice-bath
  2. temperaturecooling
  3. customthe resultant precipitate was removed by filtration
  4. customthe solvent was evaporated in vacuo
  5. additionThe residue was mixed with saturated aqueous sodium hydrogen carbonate (10.0 ml)
  6. extractionthe mixture was extracted with chloroform (20.0 ml)
  7. washThe extract was washed with water
  8. dry with materialdried over magnesium sulfate
  9. customevaporated in vacuo
  10. customThe residue was recrystallized from a mixture of methanol and acetone

출처 및 근거

ORD 기록
ord-0003897d204849bf86b2e0ba626abee7
출처 데이터셋
uspto-grants-1988_08
특허 번호
US04764514

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