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

HRID 20277
Notes
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Reaction equation

HRID 20277 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-e59ae674d51d457999a3180b2ce91eb5
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07745630B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes