4-Fluoroaniline → N-[(1-acetyl-4-piperidinyl)methyl]-N'-(4-fluorophenyl)thiourea

HRID 579783Notes

Reaction equation

HRID 579783 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][N:11]=[C:12]=[S:13])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[F:14][C:15]1[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=1>O1CCCC1>[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][NH:11][C:12]([NH:21][C:18]2[CH:19]=[CH:20][C:15]([F:14])=[CH:16][CH:17]=2)=[S:13])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 97314-FluoroanilineHCID 156115901-Acetyl-4-(isothiocyanatomethyl)piperidine

Product 1

HCID 15611591N-[(1-acetyl-4-piperidinyl)methyl]-N'-(4-fluorophenyl)thioureaYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4 parts of 1-acetyl-4-(isothiocyanatomethyl)piperidine, 2.2 parts of 4-fluorobenzenamine and 90 parts of tetrahydrofuran was stirred overnight at reflux temperature. The reaction mixture was evaporated, yielding 6.2 parts (100%) of N-[(1-acetyl-4-piperidinyl)methyl]-N'-(4-fluorophenyl)thiourea as a residue (intermediate 12).

Workup

  1. temperatureat reflux temperature
  2. customThe reaction mixture was evaporated

Sources & evidence

ORD record
ord-6ba11a5ef6d04607a33326e97ca1103c
Source dataset
uspto-grants-1988_06
Patent number
US04749702

Reaction notes

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