N-bromobutanimide → 2-BROMO-5-(4-METHYL-PIPERAZIN-1-YL)-BENZALDEHYDE

HRID 1989814Notes

Reaction equation

HRID 1989814 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=2)[CH:11]=[O:12])[CH2:4][CH2:3]1.[Br:16]N1C(=O)CCC1=O>C(Cl)Cl>[Br:16][C:13]1[CH:14]=[CH:15][C:8]([N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)=[CH:9][C:10]=1[CH:11]=[O:12]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 263388043-(4-Methylpiperazin-1-yl)benzaldehyde

Product 1

HCID 114033292-BROMO-5-(4-METHYL-PIPERAZIN-1-YL)-BENZALDEHYDEYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-(4-Methyl-piperazin-1-yl)-benzaldehyde (49 mmol) in methylene chloride (150 ml) was slowly (30 min) added a solution of N-bromosuccinimide (98 mmol) in methylene chloride (450 ml). The mixture was stirred for 10 min, washed with 2M sodium hydroxide and the organic phase was removed under reduced pressure. The resulting oil was purified by column chromatography giving the title compound as 90% pure black oil in 95% yield (the impurity being 4-bromo-3-(4-methyl-piperazin-1-yl)-benzaldehyde).

Workup

  1. custom(30 min)
  2. washwashed with 2M sodium hydroxide
  3. customthe organic phase was removed under reduced pressure
  4. customThe resulting oil was purified by column chromatography

Sources & evidence

ORD record
ord-e5a84479f06b4807a0e9b1752f35876f
Source dataset
uspto-grants-2010_01
Patent number
US07642367B2

Reaction notes

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