Acetic Acid → HCID 20298778, compound

HRID 1448100Notes

Reaction equation

HRID 1448100 reaction equation
Cl.Cl.[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:31])[CH2:11][N:12]2[CH2:17][CH2:16][N:15]([CH:18]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:14][CH2:13]2)=[CH:6][C:5]=1[N+:32]([O-:34])=[O:33].CO.[BH4-].[Na+].C(O)(=O)C>O>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([OH:31])[CH2:11][N:12]2[CH2:17][CH2:16][N:15]([CH:18]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:14][CH2:13]2)=[CH:6][C:5]=1[N+:32]([O-:34])=[O:33]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 4311764Sodium borohydrideHCID 20298725HCID 20298725, compound

Product 1

HCID 20298778HCID 20298778, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture of 5.2 parts of 1-(4-chloro-3-nitrophenyl)-2-[4-(diphenylmethyl)-1-piperazinyl]ethanone dihydrochloride in 40 parts of methanol are added portionwise 0.76 parts of sodium borohydride. Upon completion, stirring is continued for 30 minutes at room temperature. The reaction mixture is decomposed by the addition of a mixture of 2 parts of acetic acid and 10 parts of water. The solvent is evaporated and 50 parts of water are added to the residue. The whole is alkalized with ammonium hydroxide. The precipitated product is filtered off, washed with water and with a small amount of 2-propanol, and crystallized from ethanol, yielding 4.3 parts (95.1%) of α-(4-chloro-3-nitrophenyl)-4-(diphenylmethyl)-1-piperazineethanol; mp. 163.4° C.

Workup

  1. customThe solvent is evaporated
  2. addition50 parts of water are added to the residue
  3. filtrationThe precipitated product is filtered off
  4. washwashed with water and with a small amount of 2-propanol
  5. customcrystallized from ethanol

Sources & evidence

ORD record
ord-4fe85d12cc1c407c84ea03d8cf6bb0ea
Source dataset
uspto-grants-1979_12
Patent number
US04179505

Reaction notes

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