Triethylamine → 1-(4-Bromobenzoyl)-4-methylpiperazine

HRID 2383604Notes

Reaction equation

HRID 2383604 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.CCN(CC)CC.[Br:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1>C(Cl)Cl>[Br:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)=[O:21])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 685154-Bromobenzoyl chloride

Product 1

HCID 44643521-(4-Bromobenzoyl)-4-methylpiperazineYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of N-methylpiperizine (1.00 g, 10 mmol) and Et3N (2.1 mL, 15 mmol) in CH2Cl2 (50 mL) at rt was added 4-bromobenzoyl chloride (2.195 g, 10 mmol) in one portion. The reaction was heated to reflux briefly and cooled. The resulting mixture was stirred O/N at rt. The reaction was quenched with H2O (30 mL) and sat. NaHCO3 (10 mL), separated and dried (Na2SO4). Evaporation of solvents afforded the title compound as a pale yellowish white solid (2.69 g, 95%). 1H NMR (400 MHz, CDCl3) δ 7.64 (d, J=8.4 Hz, 2H), 7.33 (d, J=8.4 Hz, 2H), 3.70-3.20 (m, 4H), 2.40-2.15 (m, 7H; s, 3H at 2.18 ppm and m, 4H overlapping); MS ESI 283.0[M+H]+, calcd. for [C12H15BrN2O+H]+ 283.0.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux briefly
  3. temperaturecooled
  4. customThe reaction was quenched with H2O (30 mL) and sat. NaHCO3 (10 mL)
  5. customseparated
  6. dry with materialdried (Na2SO4)
  7. customEvaporation of solvents

Sources & evidence

ORD record
ord-d397064f50a24a9cadc3aa8c7b85ece0
Source dataset
uspto-grants-2012_09
Patent number
US08263596B2

Reaction notes

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