p-Anisoyl chloride → 1-[3-(4-Methoxybenzoylamino)propyl]-4-benzhydrylpiperazine

HRID 280853Notes

Reaction equation

HRID 280853 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(N(CC)CC)C.[CH3:31][O:32][C:33]1[CH:41]=[CH:40][C:36]([C:37](Cl)=[O:38])=[CH:35][CH:34]=1>C(Cl)(Cl)Cl>[CH3:31][O:32][C:33]1[CH:41]=[CH:40][C:36]([C:37]([NH:1][CH2:2][CH2:3][CH2:4][N:5]2[CH2:6][CH2:7][N:8]([CH:11]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:9][CH2:10]2)=[O:38])=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 7477p-Anisoyl chlorideHCID 8471TriethylamineHCID 137677783-(4-Benzhydryl-1-piperazinyl)-1-propanamine

Product 1

HCID 133628341-[3-(4-Methoxybenzoylamino)propyl]-4-benzhydrylpiperazineYield 49.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 1-(3-aminopropyl)-4-benzhydrylpiperazine (1.55 g) and triethylamine (0.7 ml) in chloroform (15 ml) was dropwise added p-methoxybenzoyl chloride (0.85 g) at ambient temperature with stirring, which was continued for 20 minutes. The reaction mixture was washed successively with aqueous sodium bicarbonate and water. The organic layer was separated, dried and evaporated in vacuo. The resultant oily product was subjected to column chromatography on silica gel eluting with ethyl acetate. The fractions containing the desired compound were combined and evaporated in vacuo. The residue was crystallized from a mixture of ethyl acetate and hexane to give 1-[3-(4-methoxybenzoylamino)propyl]-4-benzhydrylpiperazine (1.1 g) as white crystals. mp: 126°-128° C.

Workup

  1. customat ambient temperature
  2. washThe reaction mixture was washed successively with aqueous sodium bicarbonate and water
  3. customThe organic layer was separated
  4. customdried
  5. customevaporated in vacuo
  6. additionThe fractions containing the desired compound
  7. customevaporated in vacuo
  8. customThe residue was crystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-45435e028d2149abb3c42f25079f2be1
Source dataset
uspto-grants-1986_05
Patent number
US04591590

Reaction notes

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