Ethyl 4-isothiocyanatopiperidine-1-carboxylate → Ethyl 4-[[[[4-[[(4-fluorophenyl)methyl]amino]-3-pyridinyl]-amino]thioxomethyl]amino]-1-piperidinecarboxylate

HRID 280330Notes

Reaction equation

HRID 280330 reaction equation
[N:1]([CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:6][CH2:5]1)=[C:2]=[S:3].[F:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][NH:23][C:24]2[CH:29]=[CH:28][N:27]=[CH:26][C:25]=2[NH2:30])=[CH:18][CH:17]=1>O1CCCC1>[F:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][NH:23][C:24]2[CH:29]=[CH:28][N:27]=[CH:26][C:25]=2[NH:30][C:2]([NH:1][CH:4]2[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:6][CH2:5]2)=[S:3])=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 3018454Ethyl 4-isothiocyanatopiperidine-1-carboxylateHCID 13587968(3-Amino(4-pyridyl))[(4-fluorophenyl)methyl]amine

Product 1

HCID 13587974Ethyl 4-[[[[4-[[(4-fluorophenyl)methyl]amino]-3-pyridinyl]-amino]thioxomethyl]amino]-1-piperidinecarboxylateYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 84.7 parts of ethyl 4-isothiocyanato-1-piperidinecarboxylate, 86.8 parts of N4 -[(4-fluorophenyl)-methyl]-3,4-pyridinediamine and 450 parts of tetrahydrofuran was stirred and refluxed for 3 hours. The reaction mixture was evaporated and the residue was crystallized from acetonitrile, yielding 90 parts (52%) of ethyl 4-[[[[4-[[(4-fluorophenyl)methyl]amino]-3-pyridinyl]-amino]thioxomethyl]amino]-1-piperidinecarboxylate; mp. 166° C. (15).

Workup

  1. temperaturerefluxed for 3 hours
  2. customThe reaction mixture was evaporated
  3. customthe residue was crystallized from acetonitrile

Sources & evidence

ORD record
ord-69aa15aa9eb04b2fb25e149d3e50c697
Source dataset
uspto-grants-1986_05
Patent number
US04588722

Reaction notes

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