1-(chloro(phenyl)methyl)-3-(trifluoromethyl)benzene → HCID 57682606, compound

HRID 1926668Notes

Reaction equation

HRID 1926668 reaction equation
[CH3:1][C@@H:2]1[CH2:7][NH:6][CH2:5][CH2:4][NH:3]1.Cl[CH:9]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=1>CC#N>[CH3:1][C@H:2]1[NH:3][CH2:4][CH2:5][N:6]([CH:9]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)[CH2:7]1

Participants

4

Reactant 2

HCID 5968291-(chloro(phenyl)methyl)-3-(trifluoromethyl)benzeneHCID 73304342-Methylpiperazine, (R)-

Product 1

HCID 57682606HCID 57682606, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of (R)-(−)-2-methylpiperazine (2.2 g, 22 mmol) in CH3CN (20 mL) was added 1-(chloro(phenyl)methyl)-3-(trifluoromethyl)benzene (2.0 g, 7.4 mmol) and heated to 100° C. for 12 h and concentrated under vacuum. The residue was dissolved in CH2Cl2 (150 mL) and washed with 1N NaOH (150 mL). The organic layer was dried with K2CO3 or Na2SO4, filtered, and concentrated. The crude product was purified by ISCO using 0-20% 2N NH3/MeOH solution in CH2Cl2 to give the title compound (2.00 g, 81% yield) as oil. MS (ESI, pos. ion) m/z: 335.1 (M+1).

Workup

  1. concentrationconcentrated under vacuum
  2. dissolutionThe residue was dissolved in CH2Cl2 (150 mL)
  3. washwashed with 1N NaOH (150 mL)
  4. dry with materialThe organic layer was dried with K2CO3 or Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by ISCO

Sources & evidence

ORD record
ord-d2740a702f9d4d3c9502978fe9492151
Source dataset
uspto-grants-2012_05
Patent number
US08183244B2

Reaction notes

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