1-Methylpiperazine → 1-[6-Chloro-4-(trifluoromethyl)-2-pyridinyl]-4-methylpiperazine

HRID 2200187Notes

Reaction equation

HRID 2200187 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[N:3]=1.CCN(C(C)C)C(C)C.[CH3:22][N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>CN(C=O)C>[Cl:12][C:4]1[N:3]=[C:2]([N:26]2[CH2:27][CH2:28][N:23]([CH3:22])[CH2:24][CH2:25]2)[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=1

Participants

5

Reactant 3

HCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 5209682,6-Dichloro-4-(trifluoromethyl)pyridine

Product 1

HCID 900202451-[6-Chloro-4-(trifluoromethyl)-2-pyridinyl]-4-methylpiperazineYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dissolve 2,6-dichloro-4-(trifluoromethyl)pyridine (215 mg, 1 mmol) and DIEA (129 mg, 1 mmol) in DMF (2 mL), add 1-methyl piperazine (100 mg, 1 mmol). Stir the reaction at 120° C. overnight. Cool to room temperature; concentrate under reduced pressure to give the crude product. Purification by chromatography (silica gel, MeOH:DCM=1:10) affords the product (253 mg, 91%). MS: (M+1): 280.

Workup

  1. customthe reaction at 120° C. overnight
  2. concentrationconcentrate under reduced pressure
  3. customto give the crude product
  4. customPurification by chromatography (silica gel, MeOH:DCM=1:10)

Sources & evidence

ORD record
ord-fa8e4b37bd45471b8374175316865f2c
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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