Ammonium Chloride → HCID 54473583, compound

HRID 2288190Notes

Reaction equation

HRID 2288190 reaction equation
[F:1][C:2]([F:41])([F:40])[C:3]1[CH:4]=[C:5]([CH:33]=[CH:34][C:35]=1C(F)(F)F)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=2)[CH2:10][C@H:9]1[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([Cl:32])[CH:26]=1)=[O:7].[Cl-].[NH4+]>C(O)C.O.[Fe]>[NH2:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][N:11]2[CH2:12][CH2:13][N:8]([C:6](=[O:7])[C:5]3[CH:4]=[C:3]([C:2]([F:1])([F:40])[F:41])[CH:35]=[C:34]([C:2]([F:41])([F:40])[F:1])[CH:33]=3)[C@H:9]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([Cl:32])[CH:26]=3)[CH2:10]2)=[CH:16][CH:17]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 54256257HCID 54256257, compound

Product 1

HCID 54473583HCID 54473583, compoundYield 171.9%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of (2R)-1-[3,4-bis(trifluoromethyl)benzoyl]-2-(3,4-dichlorobenzyl)-4-(4-nitrobenzyl)piperazine (157 mg), ammonium chloride (15.7 mg) and iron powder (157 mg) in a mixture of ethanol (5 ml) and water (1.25 ml) was refluxed for 1.5 hours. After cooling, the precipitates were filtered off and the filtrate was evaporated in vacuo. The residue was purified by column chromatography on silica gel with a mixture of toluene and ethyl acetate as an eluent to give (2R)-4-(4-aminobenzyl)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dichlorobenzyl)piperazine (128.4 mg).

Workup

  1. temperaturewas refluxed for 1.5 hours
  2. temperatureAfter cooling
  3. filtrationthe precipitates were filtered off
  4. customthe filtrate was evaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel with a mixture of toluene and ethyl acetate as an eluent

Sources & evidence

ORD record
ord-eaa097d612a142389b3778d8332d2919
Source dataset
uspto-grants-2000_07
Patent number
US06087357

Reaction notes

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