Dicyclohexylcarbodiimide → 1H-Indole-3-carboxamide, 5-fluoro-2-methyl-N-(1-(phenylmethyl)-4-piperidinyl)-

HRID 2290202노트

반응식

HRID 2290202 반응식
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH3:11])=[C:5]2[C:12]([OH:14])=O.[NH2:15][CH:16]1[CH2:21][CH2:20][N:19]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:18][CH2:17]1.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[CH2:22]([N:19]1[CH2:20][CH2:21][CH:16]([NH:15][C:12]([C:5]2[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=3)[NH:7][C:6]=2[CH3:11])=[O:14])[CH2:17][CH2:18]1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

참가 물질

5

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 4158521-Benzyl-4-piperidylamineHCID 135362755-fluoro-2-methyl-1H-indole-3-carboxylic acid

생성물 1

HCID 30626671H-Indole-3-carboxamide, 5-fluoro-2-methyl-N-(1-(phenylmethyl)-4-piperidinyl)-수율 74.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 16 g of 5-fluoro-2-methylindole-3-carboxylic acid in 260 ml of tetrahydrofuran were added 16 g of 4-amino-1-benzylpiperidine and 19 g of dicyclohexylcarbodiimide, and the whole mixture was refluxed under heating for 3 hours. After cooling, the precipitated dicyclohexylurea was filtered off and the extract was concentrated. A mixture of the residue in 70 ml of tetrahydrofuran was stirred at room temperature and the insoluble dicyclohexylurea was filtered off. The filtrate was concentrated and the resulting residue was crystallized with hexane. The resultant crystals were filtered with suction and recrystallized from ethyl acetate to give 22.5 g of N-(1-benzyl-4-piperidyl)-5-fluoro-2-methylindole-3-carboxamide, melting at 166°-169° C.

후처리

  1. temperaturethe whole mixture was refluxed
  2. temperatureunder heating for 3 hours
  3. temperatureAfter cooling
  4. filtrationthe precipitated dicyclohexylurea was filtered off
  5. concentrationthe extract was concentrated
  6. additionA mixture of the residue in 70 ml of tetrahydrofuran
  7. filtrationthe insoluble dicyclohexylurea was filtered off
  8. concentrationThe filtrate was concentrated
  9. customthe resulting residue was crystallized with hexane
  10. filtrationThe resultant crystals were filtered with suction
  11. customrecrystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-9bb778fe7e9944459327a8dc48f6cce4
출처 데이터셋
uspto-grants-1986_10
특허 번호
US04616009

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