1-Phenylpiperazine → 1-(naphthalen-2-ylmethyl)-4-phenylpiperazine

HRID 1288565Notes

Reaction equation

HRID 1288565 reaction equation
Cl[CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH:19]1[CH:20]=[CH:21][C:22]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[CH:23][CH:24]=1>CN(C)C=O>[CH:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:11]=[CH:12][C:3]=1[CH2:2][N:28]1[CH2:29][CH2:30][N:25]([C:22]2[CH:23]=[CH:24][CH:19]=[CH:20][CH:21]=2)[CH2:26][CH2:27]1

Participants

5

Reactant 3

HCID 70961-PhenylpiperazineHCID 10340Sodium CarbonateHCID 756322-(Chloromethyl)naphthalene

Product 1

HCID 2878041-(naphthalen-2-ylmethyl)-4-phenylpiperazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 10.0 g. of β-chloromethylnapthalene, 6.0 g. of sodium carbonate and 9.0 g. of phenylpiperazine in 60 ml. of dimethylformamide is stirred under nitrogen on a steambath for five hours. The reaction mixture is then cooled and filtered. The filtrate is concentrated and stirred with ice water. The formed precipitate is filtered off, dissolved in isobutyl alcohol and treated with ethereal hydrogen chloride to yield the hydrochloride salt of 1-(β-napthylmethyl)-4-(phenyl)piperazine having a melting point of 226°-228° C.

Workup

  1. additionA mixture of 10.0 g
  2. temperatureThe reaction mixture is then cooled
  3. filtrationfiltered
  4. concentrationThe filtrate is concentrated
  5. filtrationThe formed precipitate is filtered off
  6. dissolutiondissolved in isobutyl alcohol
  7. additiontreated with ethereal hydrogen chloride

Sources & evidence

ORD record
ord-b50ac38330f74f7494d55c0576370cb9
Source dataset
uspto-grants-1976_10
Patent number
US03988457

Reaction notes

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