Water → 1-(4-Benzylpiperazin-1-yl)-4-chlorobutan-1-one

HRID 1388324Notes

Reaction equation

HRID 1388324 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:21][CH:22](C)[CH2:23][CH2:24][C:25](Cl)=[O:26].O>C(Cl)Cl>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:25](=[O:26])[CH2:24][CH2:23][CH2:22][Cl:21])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 759941-BenzylpiperazineHCID 126039624-Chloropentanoyl chloride

Product 1

HCID 43809961-(4-Benzylpiperazin-1-yl)-4-chlorobutan-1-oneYield 57.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-Benzylpiperazine (1.0 g, 5.7 mmole) and triethylamine (1.17 ml, 8.5 mmole) were combined in 20 ml of methylene chloride. 4-Chlorovaleryl chloride (0.945 ml, 8.5 mmole) in 10 ml of methylene chloride was added dropwise over 20 minutes and the reaction mixture stirred for 16 hours at room temperature. Water (20 ml) was then added and the organic layer dried (anhydrous magnesium sulfate) and evaporated in vacuo to a gum. The gum was chromatographed on silica gel with ethyl acetate as eluant and tlc monitoring. Clean product fractions were combined and evaporated to yield the title product as a gum [920 mg, Rf 0.5 (ethyl acetate)].

Workup

  1. dry with materialthe organic layer dried (anhydrous magnesium sulfate)
  2. customevaporated in vacuo to a gum
  3. customThe gum was chromatographed on silica gel with ethyl acetate as eluant
  4. customevaporated

Sources & evidence

ORD record
ord-b105bf95150f4964afe737952d0f89e8
Source dataset
uspto-grants-1984_02
Patent number
US04431646

Reaction notes

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