3-(Trifluoromethyl)phenol → m-Trifluoromethylphenyl 1-amidino-4-piperidinepropionate hydrochloride

HRID 1388847Notes

Reaction equation

HRID 1388847 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]([F:26])([F:25])[C:18]1[CH:19]=[C:20](O)[CH:21]=[CH:22][CH:23]=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:22]2[CH:21]=[CH:20][CH:19]=[C:18]([C:17]([F:26])([F:25])[F:16])[CH:23]=2)=[O:14])[CH2:7][CH2:6]1)(=[NH:3])[NH2:4]

Participants

5

Reactant 3

HCID 73763-(Trifluoromethyl)phenolHCID 10868DicyclohexylcarbodiimideHCID 155835121-Amidino-4-piperidinepropionic acid hydrochloride

Product 1

HCID 70508313m-Trifluoromethylphenyl 1-amidino-4-piperidinepropionate hydrochlorideYield 62.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 4.0 g of 1-amidino-4-piperidinepropionic acid hydrochloride and 2.75 g of m-trifluoromethylphenol was suspended in 27 ml of dry pyridine. To the suspension was added 3.5 g of dicyclohexylcarbodiimide, and the resulting mixture was stirred at room temperature for 6 hours. After removal of any insoluble materials, the solvent was removed. The residue was washed with ether, dissolved in chloroform and then stirred. After removal of any insoluble materials, the filtrate was washed twice with a saturated sodium chloride solution and then dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to obtain 4.0 g (yield: 62.0%) of m-trifluoromethylphenyl 1-amidino-4-piperidinepropionate hydrochloride as colorless crystals having a melting point of 97° to 100° C.

Workup

  1. customAfter removal of any insoluble materials
  2. customthe solvent was removed
  3. washThe residue was washed with ether
  4. dissolutiondissolved in chloroform
  5. stirringstirred
  6. customAfter removal of any insoluble materials
  7. washthe filtrate was washed twice with a saturated sodium chloride solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-cd0940ffb03942e794163208124b35a5
Source dataset
uspto-grants-1984_02
Patent number
US04433152

Reaction notes

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