Triethylamine → N-(4-chlorophenyl)-4-cyano-4-phenylpiperidine-1-carbothioamide

HRID 419848Notes

Reaction equation

HRID 419848 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]=[C:16]=[S:17])=[CH:11][CH:10]=1.Cl.[C:19]([C:21]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)#[N:20]>ClCCl>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([N:24]2[CH2:25][CH2:26][C:21]([C:19]#[N:20])([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH2:22][CH2:23]2)=[S:17])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 164804-Chlorophenyl isothiocyanateHCID 30849734-Phenylpiperidine-4-carbonitrile hydrochloride

Product 1

HCID 3875011N-(4-chlorophenyl)-4-cyano-4-phenylpiperidine-1-carbothioamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (1.4 mL, 10 mmol) was added to a suspension of 4-chlorophenyl isothiocyanate (1.69 g, 10 mmol) and 4-cyano-4-phenylpiperidine hydrochloride (2.22 g, 10 mmol) in dichloromethane (100 mL), and the reaction was then stirred at room temperature for 20 minutes. The mixture was washed with 2N hydrochloric acid, then brine, it was dried over MgSO4 and evaporated under reduced pressure to afford the title compound as a white solid, 3.62 g.

Workup

  1. washThe mixture was washed with 2N hydrochloric acid
  2. dry with materialbrine, it was dried over MgSO4
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-8d45db7500a44885ac523e287da83c8e
Source dataset
uspto-grants-2012_01
Patent number
US08093400B2

Reaction notes

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