Dimethylformamide → HCID 70509339, compound

HRID 1388852Notes

Reaction equation

HRID 1388852 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].[CH3:16][O:17][C:18]([C:20]1[CH:21]=[CH:22][C:23](O)=[CH:24][CH:25]=1)=[O:19].C1(N=C=NC2CCCCC2)CCCCC1.CN(C)C=O>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:23]2[CH:22]=[CH:21][C:20]([C:18]([O:17][CH3:16])=[O:19])=[CH:25][CH:24]=2)=[O:14])[CH2:7][CH2:6]1)(=[NH:3])[NH2:4]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7456MethylparabenHCID 10868DicyclohexylcarbodiimideHCID 155835121-Amidino-4-piperidinepropionic acid hydrochloride

Product 1

HCID 70509339HCID 70509339, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 5 g of 1-amidino-4-piperidinepropionic acid hydrochloride, 3.23 g of methyl p-hydroxybenzoate, 4.38 g of dicyclohexylcarbodiimide, 100 ml of dry dimethylformamide and 20 ml of dry pyridine was stirred at room temperature for 24 hours, and the mixture was treated in the same procedure as in Example 11. The crystals obtained were recrystallized from isopropanolether to obtain 5.7 g (yield: 72.7%) of p-methoxycarbonylphenyl 1-amidino-4-piperidinepropionate hydrochloride as colorless needles having a melting point of 163° to 164.5° C.

Workup

  1. additionthe mixture was treated in the same procedure as in Example 11
  2. customThe crystals obtained
  3. customwere recrystallized from isopropanolether

Sources & evidence

ORD record
ord-cc179eceb8ed4fc99e80b6034db5d728
Source dataset
uspto-grants-1984_02
Patent number
US04433152

Reaction notes

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