Water → HCID 86751313, compound

HRID 1418577Notes

Reaction equation

HRID 1418577 reaction equation
[F:1][C:2]([F:42])([F:41])[C:3]1[CH:4]=[C:5]([CH:34]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:36]=1)[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[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[NH:27][CH:26]=1)=[O:7].[Cl-].[NH4+].O>C(O)C.[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:34]=[C:35]([C:37]([F:38])([F:39])[F:40])[CH:36]=[C:3]([C:2]([F:42])([F:41])[F:1])[CH:4]=3)[C@H:9]([CH2:24][C:25]3[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[NH:27][CH:26]=3)[CH2:10]2)=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 86751314HCID 86751314, compound

Product 1

HCID 86751313HCID 86751313, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

A mixture of (2R)-1-[3,5-bis(trifluoromethyl)-benzoyl]-2-(1H-indol-3-yl-methyl)-4-(4-nitrobenzyl)-piperazine (360 mg), iron powder (360 mg), ammonium chloride (36 mg) and water (1.5 ml) in ethanol (6 ml) was heated under reflux for 40 minutes. After cooling, the reaction mixture was filtered and the filtrate was evaporated under reduced pressure. The residue was purified by column chromatography on a silica gel eluting with a mixture of dichloromethane and methanol (10:1) to give (2R)-4-(4-aminobenzyl)-1-[3,5-bis(trifluoromethyl)-benzoyl]-2-(1H-indol-3-yl-methyl)piperazine (0.34 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 40 minutes
  3. temperatureAfter cooling
  4. filtrationthe reaction mixture was filtered
  5. customthe filtrate was evaporated under reduced pressure
  6. customThe residue was purified by column chromatography on a silica gel eluting with a mixture of dichloromethane and methanol (10:1)

Sources & evidence

ORD record
ord-489692d6613b44dfbf09340a7824a2ca
Source dataset
uspto-grants-1999_03
Patent number
US05883098

Reaction notes

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