1-Benzylpiperazine → HCID 20480158, compound

HRID 1649512Notes

Reaction equation

HRID 1649512 reaction equation
C1(C)C=CC(S(O[CH2:11][CH:12]([C:14]2[CH:19]=[CH:18][C:17]([C:20](=[O:27])[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:16][CH:15]=2)[CH3:13])(=O)=O)=CC=1.[CH2:29]([N:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(#N)C>[C:20]([C:17]1[CH:16]=[CH:15][C:14]([CH:12]([CH3:13])[CH2:11][N:39]2[CH2:40][CH2:41][N:36]([CH2:29][C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH2:37][CH2:38]2)=[CH:19][CH:18]=1)(=[O:27])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 759941-BenzylpiperazineHCID 12802913HCID 12802913, compound

Product 1

HCID 20480158HCID 20480158, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Reaction of 2-(4-benzoylphenyl)propyl p-toluenesulfonate with 1-benzylpiperazine in acetonitrile and isolation of the product in the form of the free base affords 1-[2-(4-benzoylphenyl)propyl]-4-benzylpiperazine. Conversion of the latter to the ethylene glycol ketal, catalytic reduction of the latter over palladium-on-charcoal at a hydrogen pressure of 50 p.s.i. in order to effect catalytic debenzylation thereof using the manipulative procedure described in Example 10 above, cleavage of the ketal with aqueous hydrochloric acid, and isolation of the product in the form of the dihydrochloric salt affords 1-[2-(4-benzoylphenyl)propyl]piperazine dihydrochloride m.p. 243°-245° C. (from ethanol).

Sources & evidence

ORD record
ord-3ddc4e34cb404ce3907a457d4c30a1cf
Source dataset
uspto-grants-1983_11
Patent number
US04417052

Reaction notes

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