Dimethylformamide → p-Chlorophenyl 1-amidino-4-piperidinepropionate hydrochloride

HRID 1388843Notes

Reaction equation

HRID 1388843 reaction equation
Cl.[C:2]([N:5]1[CH2:10][CH2:9][CH:8]([CH2:11][CH2:12][C:13](O)=[O:14])[CH2:7][CH2:6]1)(=[NH:4])[NH2:3].[Cl:16]C1C=CC(OS([O:26][C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)=O)=CC=1.CN(C)C=O>N1C=CC=CC=1>[ClH:16].[C:2]([N:5]1[CH2:10][CH2:9][CH:8]([CH2:11][CH2:12][C:13]([O:26][C:27]2[CH:28]=[CH:29][C:30]([Cl:33])=[CH:31][CH:32]=2)=[O:14])[CH2:7][CH2:6]1)(=[NH:3])[NH2:4]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 155835121-Amidino-4-piperidinepropionic acid hydrochlorideHCID 20449815Bis-(p-chlorophenyl)sulfite

Product 1

HCID 70508251p-Chlorophenyl 1-amidino-4-piperidinepropionate hydrochlorideYield 79.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 1.5 g of 1-amidino-4-piperidinepropionic acid hydrochloride and 7.7 g of bis-(p-chlorophenyl)sulfite was stirred at room temperature for 30 minutes in a solution of 12 ml of dry dimethylformamide and 6 ml of dry pyridine. The solvent was removed under reduced pressure, and ether was added to the residue to give crystals. The crystals were washed with ether twice and then with ethyl acetate and recrystallized from methanol-ether to obtain 1.75 g (yield: 79.5%) of p-chlorophenyl 1-amidino-4-piperidinepropionate hydrochloride as colorless crystals having a melting point of 173° to 176° C.

Workup

  1. customThe solvent was removed under reduced pressure, and ether
  2. additionwas added to the residue
  3. customto give crystals
  4. washThe crystals were washed with ether twice
  5. customwith ethyl acetate and recrystallized from methanol-ether

Sources & evidence

ORD record
ord-9b03bc7f767c416a8ec001ea1cb8cfab
Source dataset
uspto-grants-1984_02
Patent number
US04433152

Reaction notes

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