Benzhydrylpiperazine → HCID 20298725, compound

HRID 1389312Notes

Reaction equation

HRID 1389312 reaction equation
[C:1]1([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:21][C:22]([C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([N+:31]([O-:33])=[O:32])[CH:25]=1)=[O:23]>CC(=O)C>[ClH:30].[ClH:30].[Cl:30][C:27]1[CH:28]=[CH:29][C:24]([C:22](=[O:23])[CH2:21][N:11]2[CH2:10][CH2:9][N:8]([CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:13][CH2:12]2)=[CH:25][C:26]=1[N+:31]([O-:33])=[O:32]

Participants

4

Reactant 2

HCID 70048BenzhydrylpiperazineHCID 27783302-Bromo-1-(4-chloro-3-nitrophenyl)ethan-1-one

Product 1

HCID 20298725HCID 20298725, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 13.9 parts of 1-(diphenylmethyl)piperazine, 8.35 parts of 2-bromo-1-(4-chloro-3-nitrophenyl)ethanone and 40 parts of 2-propanone is stirred for 30 minutes at room temperature. The formed precipitate is filtered off and 210 parts of 2,2'-oxybispropane are added to the filtrate. The whole is treated with activated charcoal. The latter is filtered off and an excess of 2-propanol, previously saturated with gaseous hydrogen chloride, is added to the filtrate. The formed hydrochloride salt is filtered off, stirred in 80 parts of 2-propanol, filtered off again and crystallized from ethanol. The product is filtered off and recrystallized from 2-methoxyethanol, yielding 6.4 parts of 1-(4-chloro-3-nitrophenyl)-2-[4-(diphenylmethyl)-1-piperazinyl]ethanone dihydrochloride; mp. 165° C.

Workup

  1. filtrationThe formed precipitate is filtered off
  2. addition210 parts of 2,2'-oxybispropane are added to the filtrate
  3. additionThe whole is treated with activated charcoal
  4. filtrationThe latter is filtered off
  5. additionan excess of 2-propanol, previously saturated with gaseous hydrogen chloride, is added to the filtrate
  6. filtrationThe formed hydrochloride salt is filtered off
  7. stirringstirred in 80 parts of 2-propanol
  8. filtrationfiltered off again
  9. customcrystallized from ethanol
  10. filtrationThe product is filtered off
  11. customrecrystallized from 2-methoxyethanol

Sources & evidence

ORD record
ord-80e2322f21844fcc833bb01df9814cdb
Source dataset
uspto-grants-1981_01
Patent number
US04243806

Reaction notes

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