4-Fluorophenol → p-Fluorophenyl 1-amidino-4-piperidinepropionate hydrochloride

HRID 1388845Notes

Reaction equation

HRID 1388845 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].[F:16][C:17]1[CH:22]=[CH:21][C:20](O)=[CH:19][CH:18]=1.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:20]2[CH:21]=[CH:22][C:17]([F:16])=[CH:18][CH:19]=2)=[O:14])[CH2:7][CH2:6]1)(=[NH:3])[NH2:4]

Participants

5

Reactant 3

HCID 97324-FluorophenolHCID 10868DicyclohexylcarbodiimideHCID 155835121-Amidino-4-piperidinepropionic acid hydrochloride

Product 1

HCID 70508684p-Fluorophenyl 1-amidino-4-piperidinepropionate hydrochlorideYield 50.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 2.00 g of 1-amidino-4-piperidinepropionic acid hydrochloride and 0.95 g of p-fluorophenol was suspended in 20 ml of dry pyridine. To the suspension was added with stirring and ice-cooling 1.74 g of dicyclohexylcarbodiimide and the resulting mixture was allowed to stand at room temperature for 4 days. After removal of any insoluble materials, the filtrate was concentrated under reduced pressure. Ethyl acetate was added to the residue to give crystals which were then recrystallized from methanol-ether to obtain 1.4 g (yield: 50.0%) of p-fluorophenyl 1-amidino-4-piperidinepropionate hydrochloride as colorless crystals having a melting point of 131° to 133° C.

Workup

  1. additionTo the suspension was added
  2. customAfter removal of any insoluble materials
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionEthyl acetate was added to the residue
  5. customto give crystals which
  6. customwere then recrystallized from methanol-ether

Sources & evidence

ORD record
ord-f386404dc3e748dc8dc8a5909c44a0aa
Source dataset
uspto-grants-1984_02
Patent number
US04433152

Reaction notes

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