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

HRID 1388856Notes

Reaction equation

HRID 1388856 reaction equation
Cl.[C:2]([N:5]1[CH2:10][CH2:9][CH:8]([C:11](O)=[O:12])[CH2:7][CH2:6]1)(=[NH:4])[NH2:3].[Cl:14]C1C=CC(OS([O:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)=O)=CC=1.CN(C)C=O>N1C=CC=CC=1>[ClH:14].[C:2]([N:5]1[CH2:10][CH2:9][CH:8]([C:11]([O:24][C:25]2[CH:26]=[CH:27][C:28]([Cl:31])=[CH:29][CH:30]=2)=[O:12])[CH2:7][CH2:6]1)(=[NH:3])[NH2:4]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 20449815Bis-(p-chlorophenyl)sulfiteHCID 700438971-Amidino-4-piperidinecarboxylic acid hydrochloride

Product 1

HCID 20470413p-Chlorophenyl 1-amidino-4-piperidinecarboxylate hydrochlorideYield 70.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 1.5 g of 1-amidino-4-piperidinecarboxylic acid hydrochloride and 8.8 g of bis-(p-chlorophenyl)sulfite was stirred at room temperature for 1 hour in a solution of 14 ml of dry dimethylformamide and 7 ml of dry pyridine. The solvent was removed under reduced pressure, and the residue was washed twice with dry ether. Acetone was added to the residue to give crystals. The crystals were washed with ether and then with ethyl acetate and recrystallized from methanol-ether to obtain 1.62 g (yield: 70.4%) of p-chlorophenyl 1-amidino-4-piperidinecarboxylate hydrochloride as colorless crystals having a melting point of 196° to 198° C.

Workup

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

Sources & evidence

ORD record
ord-3006300221724cdba5c1c591ffadd2f9
Source dataset
uspto-grants-1984_02
Patent number
US04433152

Reaction notes

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