4-Hydroxybenzaldehyde → p-Formylphenyl 1-amidino-4-piperidinepropionate hydrochloride

HRID 1388848Notes

Reaction equation

HRID 1388848 reaction equation
[ClH:1].[C:2]([N:5]1[CH2:10][CH2:9][CH:8]([CH2:11][CH2:12][C:13]([OH:15])=[O:14])[CH2:7][CH2:6]1)(=[NH:4])[NH2:3].O[C:17]1[CH:24]=[CH:23][C:20]([CH:21]=[O:22])=[CH:19][CH:18]=1.C1(N=C=NC2CCCCC2)CCCCC1>N1C=CC=CC=1>[ClH:1].[C:2]([N:5]1[CH2:10][CH2:9][CH:8]([CH2:11][CH2:12][C:13]([O:15][C:17]2[CH:24]=[CH:23][C:20]([CH:21]=[O:22])=[CH:19][CH:18]=2)=[O:14])[CH2:7][CH2:6]1)(=[NH:3])[NH2:4]

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 10868DicyclohexylcarbodiimideHCID 155835121-Amidino-4-piperidinepropionic acid hydrochloride

Product 1

HCID 86739279p-Formylphenyl 1-amidino-4-piperidinepropionate hydrochlorideYield 36.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 4.0 g of 1-amidino-4-piperidinepropionic acid hydrochloride and 2.1 g of p-hydroxybenzaldehyde was suspended in 20 ml of dry pyridine. 3.5 g of dicyclohexylcarbodiimide was added with stirring to the suspension, and the resulting mixture was stirred overnight at room temperature. After removal of any insoluble materials, the filtrate was concentrated under reduced pressure. Ethyl acetate was added to the residue, and the mixture was stirred to give crystals. The crystals were recrystallized from methanol-ether to obtain 2.1 g (yield: 36.4%) of p-formylphenyl 1-amidino-4-piperidinepropionate hydrochloride as colorless crystals having a melting point of 144° to 147° C.

Workup

  1. stirringthe resulting mixture was stirred overnight at room temperature
  2. customAfter removal of any insoluble materials
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionEthyl acetate was added to the residue
  5. stirringthe mixture was stirred
  6. customto give crystals
  7. customThe crystals were recrystallized from methanol-ether

Sources & evidence

ORD record
ord-5af6023b70d844b9b134f63e8d5cff30
Source dataset
uspto-grants-1984_02
Patent number
US04433152

Reaction notes

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