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

HRID 2290202ノート

反応式

HRID 2290202 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9bb778fe7e9944459327a8dc48f6cce4
出典データセット
uspto-grants-1986_10
特許番号
US04616009

反応ノート

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