Cyanuric chloride → 1-(4,6-dichloro-1,3,5-triazin-2-yl)-N-{[2-(trifluoromethyl)phenyl]methyl}-4-piperidinecarboxamide

HRID 1678417Notes

Reaction equation

HRID 1678417 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][NH:10][C:11]([CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)=[O:12].[N:21]1[C:28]([Cl:29])=[N:27][C:25](Cl)=[N:24][C:22]=1[Cl:23].C(N(C(C)C)CC)(C)C>C(#N)C>[Cl:23][C:22]1[N:21]=[C:28]([Cl:29])[N:27]=[C:25]([N:16]2[CH2:17][CH2:18][CH:13]([C:11]([NH:10][CH2:9][C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[C:2]([F:1])([F:19])[F:20])=[O:12])[CH2:14][CH2:15]2)[N:24]=1

Participants

5

Reactant 3

HCID 7954Cyanuric chlorideHCID 81531DiisopropylethylamineHCID 59614575N-{[2-(trifluoromethyl)phenyl]methyl}-4-piperidinecarboxamide

Product 1

HCID 866443151-(4,6-dichloro-1,3,5-triazin-2-yl)-N-{[2-(trifluoromethyl)phenyl]methyl}-4-piperidinecarboxamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of N-{[2-(trifluoromethyl)phenyl]methyl}-4-piperidinecarboxamide (950 mg, 3.32 mmol, 1.00 equiv) in acetonitrile (30 ml) at room temperature, cyanuric chloride (612 mg, 3.32 mmol, 1.00 equiv) and diisopropylethylamine (DIEA, 1.74 ml, 9.95 mmol, 3.00 equiv) were added dropwise. The reaction was stirred at room temperature for 3 h. Without workup or purification, the reaction mixture was carried forward to the next step. MS (ES+): m/e 435.9 [M+H]+

Workup

  1. customWithout workup or purification

Sources & evidence

ORD record
ord-2dba5bfded25437cb075a8b26a9da52b
Source dataset
uspto-grants-2011_08
Patent number
US08008483B2

Reaction notes

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