Benzyl Bromide → 1-Methyl-1-benzyl-4-[3-(4-tert.-butylphenyl)-2-methylpropyl]-piperazinium bromide

HRID 745486

Reaction equation

HRID 745486 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH:9]([CH3:21])[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:13][CH:12]=2)[CH2:4][CH2:3]1.[CH2:22]([Br:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(OCC)(=O)C>[Br-:29].[CH3:1][N+:2]1([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:7][CH2:6][N:5]([CH2:8][CH:9]([CH3:21])[CH2:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:15][CH:16]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 132519811-[3-(4-tert-Butylphenyl)-2-methylpropyl]-4-methylpiperazine

Product 1

HCID 132519821-Methyl-1-benzyl-4-[3-(4-tert.-butylphenyl)-2-methylpropyl]-piperazinium bromideYield 80.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 14.4 g of 1-methyl-4-[3-(4-tert.-butylphenyl)-2-methylpropyl]-piperazine and 10.3 g of benzyl bromide in 200 ml of ethyl acetate was refluxed for 6 hours, after which the mixture was evaporated down to 80 ml and then cooled to +5° C. The precipitated product was filtered off under suction, washed with ether and dried. 18.4 g of 1-methyl-1-benzyl-4-[3-(4-tert.-butylphenyl)-2-methylpropyl]-piperazinium bromide were obtained in the form of colorless crystals of melting point 216° C. (compound 3).

Workup

  1. customafter which the mixture was evaporated down to 80 ml
  2. temperaturecooled to +5° C
  3. filtrationThe precipitated product was filtered off under suction
  4. washwashed with ether
  5. customdried

Sources & evidence

ORD record
ord-bd19a1f8882144ec99b21925d36208f7
Source dataset
uspto-grants-1986_07
Patent number
US04599335

Linked notes

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