Cyclohexyl isothiocyanate → N-[1-[3-[2-(3-Cyclohexylthioureido)phenyl]propyl]piperidin-4-yl]-N-(p-tolyl)-2-furancarboxamide

HRID 2223898Notes

Reaction equation

HRID 2223898 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][CH:14]([N:17]([C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=2)[C:18]([C:20]2[O:21][CH:22]=[CH:23][CH:24]=2)=[O:19])[CH2:13][CH2:12]1.[CH:32]1([N:38]=[C:39]=[S:40])[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1>ClCCCl>[CH:32]1([NH:38][C:39](=[S:40])[NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[CH2:8][CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][CH:14]([N:17]([C:25]3[CH:26]=[CH:27][C:28]([CH3:31])=[CH:29][CH:30]=3)[C:18]([C:20]3[O:21][CH:22]=[CH:23][CH:24]=3)=[O:19])[CH2:15][CH2:16]2)[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1

Participants

4

Reactant 2

HCID 14289Cyclohexyl isothiocyanateHCID 59714960N-[1-[3-(2-aminophenyl)propyl]piperidin-4-yl]-N-(p-tolyl)-2-furancarboxamide

Product 1

HCID 59715053N-[1-[3-[2-(3-Cyclohexylthioureido)phenyl]propyl]piperidin-4-yl]-N-(p-tolyl)-2-furancarboxamideYield 43.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of N-[1-[3-(2-aminophenyl)propyl]piperidin-4-yl]-N-(p-tolyl)-2-furancarboxamide (0.42 g) dissolved in 1,2-dichloroethane (5 mL) was added cyclohexyl isothiocyanate (0.42 g) at room temperature. The solution was then heated under reflux for 8 hours. The solution was purified by chromatography [silica gel, dichloromethane-methanol-aqueous ammonia (97:3:0.2-95:5:0.3)] to give the title compound (0.2458 g).

Workup

  1. temperatureThe solution was then heated
  2. temperatureunder reflux for 8 hours
  3. customThe solution was purified by chromatography [silica gel, dichloromethane-methanol-aqueous ammonia (97:3:0.2-95:5:0.3)]

Sources & evidence

ORD record
ord-9cc25906e2cb470c99912d56071c4810
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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