Dicyclohexylcarbodiimide → p-Cyanophenyl 1-amidino-4-piperidinepropionate hydrochloride

HRID 1388849Notes

Reaction equation

HRID 1388849 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].[C:16]([C:18]1[CH:23]=[CH:22][C:21](O)=[CH:20][CH:19]=1)#[N:17].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:21]2[CH:22]=[CH:23][C:18]([C:16]#[N:17])=[CH:19][CH:20]=2)=[O:14])[CH2:7][CH2:6]1)(=[NH:3])[NH2:4]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 130194-CyanophenolHCID 155835121-Amidino-4-piperidinepropionic acid hydrochloride

Product 1

HCID 70509567p-Cyanophenyl 1-amidino-4-piperidinepropionate hydrochlorideYield 60.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 4.0 g of 1-amidino-4-piperidinepropionic acid hydrochloride, 2.0 g of p-cyanophenol and 3.5 g of dicyclohexylcarbodiimide was stirred overnight at room temperature in 20 ml of dry pyridine. Any insoluble materials were filtered, washed with pyridine and extracted with a solution of 20 ml of water and 20 ml of t-butanol, followed by stirring for about 20 minutes. The filtrate, washings and extract were combined together, and the solvent was removed under reduced pressure. The residue was recrystallized from water to obtain 3.4 g (yield: 59%) of p-cyanophenyl 1-amidino-4-piperidinepropionate hydrochloride as colorless crystals having a melting point of 164.5° to 169° C.

Workup

  1. filtrationAny insoluble materials were filtered
  2. washwashed with pyridine
  3. extractionextracted with a solution of 20 ml of water and 20 ml of t-butanol
  4. extractionThe filtrate, washings and extract
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was recrystallized from water

Sources & evidence

ORD record
ord-988d4d53621b4af3b2bdbc85d1018e3b
Source dataset
uspto-grants-1984_02
Patent number
US04433152

Reaction notes

Loading…