Benzoyl chloride → {4-[2-(6-Methoxynaphthalen-2-yl)propyl]piperazin-1-yl}(phenyl)methanone

HRID 1389050Notes

Reaction equation

HRID 1389050 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:10]1([CH2:16][CH:17]([C:19]2[CH:28]=[CH:27][C:26]3[C:21](=[CH:22][CH:23]=[C:24]([O:29][CH3:30])[CH:25]=3)[CH:20]=2)[CH3:18])[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.C(N1CCOCC1)C>C(Cl)Cl.CCOCC>[C:1]([N:13]1[CH2:12][CH2:11][N:10]([CH2:16][CH:17]([C:19]2[CH:28]=[CH:27][C:26]3[C:21](=[CH:22][CH:23]=[C:24]([O:29][CH3:30])[CH:25]=3)[CH:20]=2)[CH3:18])[CH2:15][CH2:14]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 7525EthylmorpholineHCID 3055305HCID 3055305, compound

Product 1

HCID 3055311{4-[2-(6-Methoxynaphthalen-2-yl)propyl]piperazin-1-yl}(phenyl)methanone

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Benzoyl chloride (0.58 ml, 5 mmols) is added, at 0° C., to a solution of 2-(2-piperazino-1-methylethyl)-6-methoxynaphthalene (1.42 g, 5 mmols) and N-ethylmorpholine (0.65 ml, 5 mmols) in 15 ml of methylene chloride. The mixture is allowed to return to ambient temperature and stirred for 3 hours. The reaction medium is washed with water and dried over sodium sulphate. Concentration of the mixture yields an oily residue which dissolves in ether and crystallises. The compound is recrystallised from ethyl acetate (15 ml).

Workup

  1. customto return to ambient temperature
  2. washThe reaction medium is washed with water
  3. dry with materialdried over sodium sulphate
  4. customConcentration of the mixture yields an oily residue which
  5. customcrystallises
  6. customThe compound is recrystallised from ethyl acetate (15 ml)

Sources & evidence

ORD record
ord-3465046ca378426fa6c710e55f2cf957
Source dataset
uspto-grants-1981_01
Patent number
US04243665

Reaction notes

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