HCID 19020615, compound → Hydrochloric Acid

HRID 1975377Notes

Reaction equation

HRID 1975377 reaction equation
[CH3:1][N:2]([CH3:39])[CH2:3][CH2:4][N:5]([C:16]1[CH:38]=[CH:37][C:19]([C:20]([N:22]2[CH2:27][CH2:26][N:25]([CH2:28][CH2:29][C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=3)[CH2:24][CH2:23]2)=[O:21])=[CH:18][CH:17]=1)C(OCC1C=CC=CC=1)=O>CO.[Pd]>[ClH:36].[ClH:36].[CH3:39][N:2]([CH3:1])[CH2:3][CH2:4][NH:5][C:16]1[CH:38]=[CH:37][C:19]([C:20]([N:22]2[CH2:23][CH2:24][N:25]([CH2:28][CH2:29][C:30]3[CH:31]=[CH:32][C:33]([Cl:36])=[CH:34][CH:35]=3)[CH2:26][CH2:27]2)=[O:21])=[CH:18][CH:17]=1

Participants

5

Reactant 1

HCID 19020615HCID 19020615, compound

Product 2

HCID 313Hydrochloric AcidHCID 19099470HCID 19099470, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1.9 g of 1-{4-[N-(2-dimethylaminoethyl)-N-benzyloxycarbonylamino]-benzoyl}-4-[2-(4-chlorophenyl)ethyl]piperazine are hydrogenated in 30 ml of methanol in the presence of 0.4 g of palladium-on-carbon. The mixture is filtered off with suction, concentrated by evaporation, rendered alkaline with 2N NaOH and extracted with ether. The mixture is concentrated by evaporation and recrystallised from ether. The 1-[4-(2-dimethylaminoethylamino)benzoyl]-4-[2-(4-chlorophenyl)ethyl]piperazine melts at 74°-78°. With alcoholic hydrochloric acid, 1-[4-(2-dimethylaminoethylamino)benzoyl]-4-[2-(4-chlorophenyl)ethyl]piperazine hydrochloride having a melting point >275° is obtained.

Workup

  1. filtrationThe mixture is filtered off with suction
  2. concentrationconcentrated by evaporation
  3. extractionextracted with ether
  4. concentrationThe mixture is concentrated by evaporation
  5. customrecrystallised from ether

Sources & evidence

ORD record
ord-d38029da55da4de9b214a412a02aaaef
Source dataset
uspto-grants-1994_02
Patent number
US05286728

Reaction notes

Loading…