Sodium borohydride → 3-{(4-Chlorophenyl)-[1-(3,5-difluorophenyl)ethylamino]methyl}phenylamine

HRID 2269460Notes

Reaction equation

HRID 2269460 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-])=O)[CH:21]=2)[NH:9][CH:10]([C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[C:14]([F:19])[CH:13]=2)[CH3:11])=[CH:4][CH:3]=1.[BH4-].[Na+]>O.O.O.O.O.O.[Ni](Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:9][CH:10]([C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[C:14]([F:19])[CH:13]=2)[CH3:11])[C:20]2[CH:21]=[C:22]([NH2:26])[CH:23]=[CH:24][CH:25]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 18334265N-[(4-Chlorophenyl)-(3-nitrophenyl)methyl]-N-[1-(3,5-difluorophenyl)ethyl]amine

Product 1

HCID 183342613-{(4-Chlorophenyl)-[1-(3,5-difluorophenyl)ethylamino]methyl}phenylamine

Reagents, catalysts & solvents 1

HCID 11791229Dichloronickel;hexahydrateCatalyst

Procedure

Following a reaction and purification procedure similar to those described in Example (59b), 2.79 g of N-[(4-chlorophenyl)-(3-nitrophenyl)methyl]-N-[1-(3,5-difluorophenyl)ethyl]amine [prepared as described in step (a) above], 3.79, of nickel chloride hexahydrate and 1.10 g of sodium borohydride were reacted, to obtain 808 mg of isomer A and 572 mg of isomer B of the title compound as colorless oils, respectively.

Workup

  1. customa reaction and purification procedure similar to
  2. customwere reacted

Sources & evidence

ORD record
ord-1784621cc6d4468c9b11f7a91e1b4a7c
Source dataset
uspto-grants-2001_12
Patent number
US06329405B1

Reaction notes

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