Dicyclohexylcarbodiimide → HCID 13536278, compound

HRID 1380325Notes

Reaction equation

HRID 1380325 reaction equation
[OH: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][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:18][CH2:17]1.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[OH: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]([NH:15][CH:16]1[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:18][CH2:17]1)=[O:14]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 11113725-Hydroxy-2-methyl-1H-indole-3-carboxylic acidHCID 10878635HCID 10878635, compound

Product 1

HCID 13536278HCID 13536278, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 3.2 g of 5-hydroxy-2-methylindole-3-carboxylic acid and 3.7 g of 4-amino-1-(3-phenylpropyl)piperidine in 60 ml of tetrahydrofuran was added 3.8 g of dicyclohexylcarbodiimide, and the whole mixture was refluxed for 2 hours. After cooling, the precipitated dicyclohexylurea was filtered off and the filtrate was concentrated. The residue was crystallized from ethyl acetate. The crystals were filtered with suction, and recrystallized from a mixture of ethyl acetate and methanol to give 5-hydroxy-2-methyl-N-[1-(3-phenylpropyl)-4-piperidyl]indole-3-carboxamide, melting at 181°-184° C. The compound was precipitated as a monohydrate at first, but the water of crystallization was evaporated by vacuum drying over 3 hours at 90° C.

Workup

  1. temperaturethe whole mixture was refluxed for 2 hours
  2. temperatureAfter cooling
  3. filtrationthe precipitated dicyclohexylurea was filtered off
  4. concentrationthe filtrate was concentrated
  5. customThe residue was crystallized from ethyl acetate
  6. filtrationThe crystals were filtered with suction
  7. customrecrystallized from a mixture of ethyl acetate and methanol

Sources & evidence

ORD record
ord-22bfdd028f8146a1bb6ac1d9a08a417d
Source dataset
uspto-grants-1986_04
Patent number
US04581355

Reaction notes

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