Benzene → 4-Methyl-1-(piperazin-1-yl)pentan-1-one

HRID 838969Notes

Reaction equation

HRID 838969 reaction equation
C([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)C1C=CC=CC=1.[CH2:14](N(CC)CC)C.[C:21](=[O:24])([O-])[O-].[K+].[K+].[CH:27]1[CH:32]=[CH:31][CH:30]=CC=1>O>[CH3:30][CH:31]([CH3:14])[CH2:32][CH2:27][C:21]([N:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)=[O:24]

Participants

6

Reactant 4

HCID 241Benzene2×HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 759941-Benzylpiperazine

Product 1

HCID 205965884-Methyl-1-(piperazin-1-yl)pentan-1-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

60 g 4-methylvaleric acid was converted to the acid chloride by heating 1 hour with 120 g thionyl chloride. Distillation gave 45.2 g (65%) 4-methyl valeroyl chloride, bp 35°-38° C/10.0 mm. This product in 100 ml benzene was added to a solution of 56 g N-benzyl piperazine and 33.8 g triethylamine in 250 ml benzene. After 1 hour at 25° a solution of 47 g potassium carbonate in 250 ml water was added. The benzene layer was removed and concentrated. The crude N-(4-methyl valeroyl) N'-benzyl piperazine was hydrogenated in 300 ml ethanol using 16 g 5% pd/catalyst. The product was distilled to give 40.2 g product, bp 110°-115° C/0.1 mm. (65%)

Workup

  1. customThe benzene layer was removed
  2. concentrationconcentrated
  3. distillationThe product was distilled

Sources & evidence

ORD record
ord-4bb85e814d564c869e8acbc7c27154e1
Source dataset
uspto-grants-1978_06
Patent number
US04093726

Reaction notes

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