4-Bromobenzoyl chloride → HCID 18357121, compound

HRID 427439Notes

Reaction equation

HRID 427439 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)=[CH:3][CH:2]=1.[Br:13][C:14]1[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][CH:15]=1>ClCCl.C(N(CC)CC)C>[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:8][CH2:9][N:10]([C:18](=[O:19])[C:17]3[CH:21]=[CH:22][C:14]([Br:13])=[CH:15][CH:16]=3)[CH2:11][CH2:12]2)=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 685154-Bromobenzoyl chlorideHCID 705171-(4-Pyridyl)piperazine

Product 1

HCID 18357121HCID 18357121, compoundYield 59.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

A solution of 1-(4-pyridyl)piperazine (0.49 g) in dry dichloromethane (20 ml) and triethylamine (0.7 ml) was treated slowly with a solution of 4-bromobenzoyl chloride (0.7 g) in dry dichloromethane (10 ml). The reaction mixture was then stirred under argon for 2 hours. The dichloromethane solvent was removed by evaporation and the residue dissolved in ethyl acetate. The organic extracts were then washed with aqueous sodium hydrogen carbonate solution, water, brine, dried (Na2SO4) and evaporated to yield a colourless oil. The residual oil was then triturated with diethyl ether and recrystallised from ethyl acetate/isohexane to give 1-(4-pyridyl)-4-(4-bromobenzoyl)piperazine (0.62 g) as a solid, m.p. 128-129° C.; microanalysis, found: C, 55.7; H, 4.7; N, 12.0%; C16H16N3OBr requires: C, 55.5; H, 4.7; N, 12.1%; NMR: (CDCl3) 3.36(s,4H), 3.73(s,4H), 6.67(dd,2H), 7.33(dd,2H), 7.58(dd,2H), 8.34(dd,2H); MS: m/z 346 (MH)+.

Workup

  1. customThe dichloromethane solvent was removed by evaporation
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washThe organic extracts were then washed with aqueous sodium hydrogen carbonate solution, water, brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customto yield a colourless oil
  7. customThe residual oil was then triturated with diethyl ether
  8. customrecrystallised from ethyl acetate/isohexane

Sources & evidence

ORD record
ord-36987e413fb244768a30e5d78693635d
Source dataset
uspto-grants-2001_11
Patent number
US06313127B1

Reaction notes

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