2,4-Dichloro-6-methyl-1,3,5-triazine → 1-(4-chloro-6-methyl-1,3,5-triazin-2-yl)-N-[(2,4-dichlorophenyl)methyl]-4-piperidinecarboxamide

HRID 1678448Notes

Reaction equation

HRID 1678448 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[C:4]([CH3:9])[N:3]=1.[Cl:10][C:11]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=1[CH2:18][NH:19][C:20]([CH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)=[O:21].C(N(C(C)C)CC)(C)C>C(#N)C>[Cl:8][C:6]1[N:5]=[C:4]([CH3:9])[N:3]=[C:2]([N:25]2[CH2:26][CH2:27][CH:22]([C:20]([NH:19][CH2:18][C:12]3[CH:13]=[CH:14][C:15]([Cl:17])=[CH:16][C:11]=3[Cl:10])=[O:21])[CH2:23][CH2:24]2)[N:7]=1

Participants

5

Reactant 3

HCID 160832,4-Dichloro-6-methyl-1,3,5-triazineHCID 81531DiisopropylethylamineHCID 20298096N-[(2,4-dichlorophenyl)methyl]-4-piperidinecarboxamide

Product 1

HCID 594477221-(4-chloro-6-methyl-1,3,5-triazin-2-yl)-N-[(2,4-dichlorophenyl)methyl]-4-piperidinecarboxamideYield 52%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a 25 mL round-bottomed flask was added 2,4-dichloro-6-methyl-1,3,5-triazine (800 mg, 2.79 mmol) and N-[(2,4-dichlorophenyl)methyl]-4-piperidinecarboxamide (859 mg, 2.79 mmol) in acetonitrile (8.7 mL). Diisopropylethylamine (1.46 mL, 8.36 mmol) was added to give a yellow suspension. The reaction mixture was stirred at room temperature for 15 minutes, at which time LC-MS showed the reaction was complete. This suspension was filtered through a Buchner funnel to afford 1-(4-chloro-6-methyl-1,3,5-triazin-2-yl)-N-[(2,4-dichlorophenyl)methyl]-4-piperidinecarboxamide (596 mg, 1.44 mmol, 52%) as a white solid which was used in the next step without further purification. MS (ES) m/e 416 [M+H]+.

Workup

  1. customto give a yellow suspension
  2. filtrationThis suspension was filtered through a Buchner funnel

Sources & evidence

ORD record
ord-3d27b8fda95c4f30a1b2c30ce13dcf71
Source dataset
uspto-grants-2011_08
Patent number
US08008483B2

Reaction notes

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