Dicyclohexylcarbodiimide → HCID 13490822, compound

HRID 2290203Notes

Reaction equation

HRID 2290203 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[C:11]([OH:13])=O.[NH2:14][CH:15]1[CH2:20][CH2:19][N:18]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:17][CH2:16]1.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[CH2:21]([N:18]1[CH2:19][CH2:20][CH:15]([NH:14][C:11]([C:5]2[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=3)[NH:7][CH:6]=2)=[O:13])[CH2:16][CH2:17]1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 4158521-Benzyl-4-piperidylamineHCID 177509305-Fluoro-1H-indole-3-carboxylic acid

Product 1

HCID 13490822HCID 13490822, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5.1 g of 5-fluoroindole-3-carboxylic acid in 150 ml of tetrahydrofuran were added 5.5 g of 4-amino-1-benzylpiperidine and 5.8 g of dicyclohexylcarbodiimide, and the whole mixture was refluxed under heating on a water bath for 3 hours. After completion of the reaction, the precipitated dicyclohexylurea and a part of the objective product were filtered and suspended in 200 ml of hot tetrahydrofuran. The suspension was stirred and the insoluble dicyclohexylurea was filtered off with suction. The combined filtrates were concentrated and the residue was crystallized with ethyl acetate. The resulting crystals were filtered to give 8.3 g of N-(1-benzyl-4-piperidyl)-5-fluoroindole-3-carboxamide. The product, when recrystallized from a mixture of ethyl acetate and ethanol, melts at 215°-217° C.

Workup

  1. temperaturethe whole mixture was refluxed
  2. temperatureunder heating on a water bath for 3 hours
  3. customAfter completion of the reaction
  4. filtrationthe precipitated dicyclohexylurea and a part of the objective product were filtered
  5. filtrationthe insoluble dicyclohexylurea was filtered off with suction
  6. concentrationThe combined filtrates were concentrated
  7. customthe residue was crystallized with ethyl acetate
  8. filtrationThe resulting crystals were filtered

Sources & evidence

ORD record
ord-7fc7769603624aba9e8d33ff7ae7b99d
Source dataset
uspto-grants-1986_10
Patent number
US04616009

Reaction notes

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