1-Phenylpiperazine → HCID 12833933, compound

HRID 1390146Notes

Reaction equation

HRID 1390146 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=O.C(N(CC)CC)C.ClC(OCC)=O.[C:23]1([N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CCOCC.C1C=CC=CC=1>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([N:32]1[CH2:33][CH2:34][N:29]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:30][CH2:31]1)=[O:9]

Participants

7

Reactant 4

HCID 70961-PhenylpiperazineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 202106-Bromohexanoic acid

Product 1

HCID 12833933HCID 12833933, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 25 g (0.128 mol) of 6-bromohexanoic acid and 12.7 g (0.125 mol) of triethylamine in 150 ml of ether was cooled (0°) and treated dropwise with 28.5 g (0.263 mol) of ethyl chloroformate. The reaction mixture was stirred for 1 hr and then filtered. To the cooled (0°) filtrate was added a solution of 21 g (0.129 mol) of N-phenylpiperazine in 50 ml of ether. The reaction mixture was then allowed to warm to room temperature for 30 min and was then washed once with 1 N NaOH solution and once with water. The dried (Na2SO4) organic layers were concentrated in vacuo to give a yellow oil which was dissolved in benzene and chromatographed on silica gel (500 g). The column was eluted with benzeneethyl acetate mixtures, the product appearing in the benzeneethyl acetate (8.5:1.5) mixtures. Evaporation of those combined mixtures gave 1-(6-bromohexanoyl)-4-phenylpiperazine.

Workup

  1. filtrationfiltered
  2. temperatureTo the cooled (0°) filtrate
  3. washwas then washed once with 1 N NaOH solution and once with water
  4. dry with materialThe dried (Na2SO4) organic layers
  5. concentrationwere concentrated in vacuo
  6. customto give a yellow oil which
  7. customchromatographed on silica gel (500 g)
  8. washThe column was eluted with benzeneethyl acetate mixtures
  9. customEvaporation of those combined mixtures

Sources & evidence

ORD record
ord-152ebb94cad945bf83cff7ac44434d91
Source dataset
uspto-grants-1981_01
Patent number
US04247710

Reaction notes

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