Hydrochloric Acid → 1-(3-Benzoylaminopropyl)-4-benzhydrylpiperazine dihydrochloride

HRID 280851Notes

Reaction equation

HRID 280851 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][N:8]([CH:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7][CH2:6]1.[C:24]([Cl:32])(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[ClH:33]>N1C=CC=CC=1.C(Cl)(Cl)Cl>[ClH:32].[ClH:33].[C:24]([NH:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][N:8]([CH:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:9][CH2:10]1)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 137677783-(4-Benzhydryl-1-piperazinyl)-1-propanamine

Product 1

HCID 233201841-(3-Benzoylaminopropyl)-4-benzhydrylpiperazine dihydrochloride

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent2×

Procedure

To a solution of 1-(3-aminopropyl)-4-benzhydrylpiperazine (1.2 g) in a mixture of pyridine (2 ml) and chloroform (15 ml) was dropwise added a solution of benzoyl chloride (0.55 ml) in chloroform (3 ml) at ambient temperature with stirring, which was continued for 1.5 hours. The reaction mixture was washed successively with aqueous sodium bicarbonate and water. The chloroform layer was separated, dried and evaporated in vacuo to give an oil. According to a conventional manner, the oil was converted to hydrochloric acid salt, which was recrystallized from a mixture of methanol and diethyl ether to afford 1-(3-benzoylaminopropyl)-4-benzhydrylpiperazine dihydrochloride (1.0 g) as white crystals. mp: 235°-237° C.

Workup

  1. washThe reaction mixture was washed successively with aqueous sodium bicarbonate and water
  2. customThe chloroform layer was separated
  3. customdried
  4. customevaporated in vacuo
  5. customto give an oil
  6. customwas recrystallized from a mixture of methanol and diethyl ether

Sources & evidence

ORD record
ord-fceeae5d0a084f80983d12bee13e820c
Source dataset
uspto-grants-1986_05
Patent number
US04591590

Reaction notes

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