1-Methylpiperazine → 1-[(3-Bromophenyl)(4-chlorophenyl)methyl]-4-methylpiperazine

HRID 845219Notes

Reaction equation

HRID 845219 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH:5](Cl)[C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1.[CH3:17][N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH:5]([N:21]1[CH2:22][CH2:23][N:18]([CH3:17])[CH2:19][CH2:20]1)[C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 201324411-Bromo-3-[chloro(4-chlorophenyl)methyl]benzene

Product 1

HCID 189559271-[(3-Bromophenyl)(4-chlorophenyl)methyl]-4-methylpiperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The benzhydryl chloride from above (8.33 g, 26.4 mmol) in 10 mL of N-methylpiperazine was heated to 110° for 12 hours under nitrogen. After cooling to room temperature, the residue was dissolved in 75 mL of methylene chloride and washed with 40 mL of 1M sodium hydroxide and two 50 mL portions of water. After drying over sodium sulfate, the solvent was removed in vacuo to give 10.2 g of 1-(3-bromo-4'-chlorobenzhydryl)-4-methylpiperazine as a dark oil. A portion of the oil was dissolved in ether and converted to the dihydrochloride salt with ethanolic hydrogen chloride. Recrystallization from 2:1 ethanol:methanol gave white powdery crystals, m.p. 229°-231°. Calc. for C18H20BrClN2.2HCl: C, 47.76; H, 4.90; N, 6.19. Found: C, 47.55; H, 4.91; N, 6.13.

Workup

  1. washwashed with 40 mL of 1M sodium hydroxide and two 50 mL portions of water
  2. dry with materialAfter drying over sodium sulfate
  3. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-aab322f587a5440d9c69f40eada708ff
Source dataset
uspto-grants-1988_07
Patent number
US04757074

Reaction notes

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