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

HRID 2269492Notes

Reaction equation

HRID 2269492 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][C@@H: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][C@@H: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 70189357N-[(4-Chlorophenyl)-(3-nitrophenyl)methyl]-N-[(R)-1-(3,5-difluorophenyl)ethyl]amine

Product 1

HCID 701892023-{(4-Chlorophenyl)-[(R)-1-(3,5-difluoropbenyl)ethylamino]methyl}phenylamineYield 98.8%

Reagents, catalysts & solvents 1

HCID 11791229Dichloronickel;hexahydrateCatalyst

Procedure

Following a similar procedure to that described in Example (1b), 1.41 g of N-[(4-chlorophenyl)-(3-nitrophenyl)methyl]-N-[(R)-1-(3,5-difluorophenyl)ethyl]amine [prepared as described in step (a) above], 1.66 g of nickel chloride hexahydrate and 558 mg of sodium borohydride were reacted, to obtain 1.29 g of the title compound as a pale yellow oil.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-b7e257fc726f48cb8aa0ae7e25fba28c
Source dataset
uspto-grants-2001_12
Patent number
US06329405B1

Reaction notes

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