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

HRID 1388846Notes

Reaction equation

HRID 1388846 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:22]=[CH:21][C:20]([S:23]([NH2:26])(=[O:25])=[O:24])=[CH:19][CH:18]=1.C1(N=C=NC2CCCCC2)CCCCC1.CN(C)C=O>CO.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:22]=[CH:21][C:20]([S:23]([NH2:26])(=[O:25])=[O:24])=[CH:19][CH:18]=2)=[O:14])[CH2:7][CH2:6]1)(=[NH:3])[NH2:4]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 10868DicyclohexylcarbodiimideHCID 74093p-HydroxybenzenesulfonamideHCID 155835121-Amidino-4-piperidinepropionic acid hydrochloride

Product 1

HCID 70508044p-Aminosulfonylphenyl 1-amidino-4-piperidinepropionate hydrochlorideYield 57.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1049PyridineSolvent

Procedure

A mixture of 4.7 g of 1-amidino-4-piperidinepropionic acid hydrochloride, 3.5 g of p-hydroxybenzene sulfonamide, 4.1 g of dicyclohexylcarbodiimide, 10 ml of dry dimethylformamide and 20 ml of dry pyridine was stirred at room temperature for 24 hours. After removal of any insoluble materials, the solvent was removed. The residue was treated with ethyl acetate and then with ether to give crystals. The crystals were dissolved in methanol, and any insoluble materials were removed by filtration. Ether was added to the filtrate to obtain 4.5 g (yield: 57.7%) of p-aminosulfonylphenyl 1-amidino-4-piperidinepropionate hydrochloride as yellow crystals having a melting point of 206° to 209° C.

Workup

  1. customAfter removal of any insoluble materials
  2. customthe solvent was removed
  3. additionThe residue was treated with ethyl acetate
  4. customwith ether to give crystals
  5. customany insoluble materials were removed by filtration
  6. additionEther was added to the filtrate

Sources & evidence

ORD record
ord-1e40797f20ca478da12c328150ba34a5
Source dataset
uspto-grants-1984_02
Patent number
US04433152

Reaction notes

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