Acetaminophen → p-Acetaminophenyl 1-amidino-4-piperidinepropionate hydrochloride

HRID 1388844Notes

Reaction equation

HRID 1388844 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].[NH:16]([C:20]1[CH:25]=[CH:24][C:23](O)=[CH:22][CH:21]=1)[C:17]([CH3:19])=[O:18].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:23]2[CH:24]=[CH:25][C:20]([NH:16][C:17]([CH3:19])=[O:18])=[CH:21][CH:22]=2)=[O:14])[CH2:7][CH2:6]1)(=[NH:3])[NH2:4]

Participants

5

Reactant 3

HCID 1983AcetaminophenHCID 10868DicyclohexylcarbodiimideHCID 155835121-Amidino-4-piperidinepropionic acid hydrochloride

Product 1

HCID 86739278p-Acetaminophenyl 1-amidino-4-piperidinepropionate hydrochlorideYield 48.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 2.0 g of 1-amidino-4-piperidinepropionic acid hydrochloride and 1.29 g of p-acetaminophenol was dissolved in 20 ml of dry pyridine. To the solution was added with stirring and ice-cooling 1.75 g of dicyclohexylcarbodiimide, and the resulting mixture was stirred overnight at room temperature. The reaction mixture was filtered to give crystals which were then washed with ethyl acetate and further with ether and dried. The crystals were refluxed with 600 ml of dichloromethane, and the resulting mixture was filtered to give an insoluble substance. The substance was washed with dichloromethane and recrystallized from methanol-ethyl acetate to obtain 1.5 g (yield: 48.4%) of p-acetaminophenyl 1-amidino-4-piperidinepropionate hydrochloride as colorless crystals having a melting point of 258° to 261° C.

Workup

  1. additionTo the solution was added
  2. stirringthe resulting mixture was stirred overnight at room temperature
  3. filtrationThe reaction mixture was filtered
  4. customto give crystals which
  5. washwere then washed with ethyl acetate and further with ether
  6. customdried
  7. temperatureThe crystals were refluxed with 600 ml of dichloromethane
  8. filtrationthe resulting mixture was filtered
  9. customto give an insoluble substance
  10. washThe substance was washed with dichloromethane
  11. customrecrystallized from methanol-ethyl acetate

Sources & evidence

ORD record
ord-33134b006fc74ad0b621829d73d7f89c
Source dataset
uspto-grants-1984_02
Patent number
US04433152

Reaction notes

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