Sodium borohydride → 3-{Phenyl-[(R)-1-(3-fluorophenyl)ethylamino]methyl}phenylamine

HRID 2269521Notes

Reaction equation

HRID 2269521 reaction equation
[C:1]1([CH:7]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-])=O)[CH:19]=2)[NH:8][C@@H:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)[CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>O.O.O.O.O.O.[Ni](Cl)Cl>[C:1]1([CH:7]([NH:8][C@@H:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)[CH3:10])[C:18]2[CH:19]=[C:20]([NH2:24])[CH:21]=[CH:22][CH:23]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 70189344N-[(R)-1-(3-Fluorophenyl)ethyl]-N-[(3-nitrophenyl)phenylmethyl]amine

Product 1

HCID 701881113-{Phenyl-[(R)-1-(3-fluorophenyl)ethylamino]methyl}phenylamineYield 92.6%

Reagents, catalysts & solvents 1

HCID 11791229Dichloronickel;hexahydrateCatalyst

Procedure

Following a procedure similar to that described in Example (1b), 1.37 g of N-[phenyl-(3-nitrophenyl)methyl]-N-[(R)-1-(3-fluorophenyl)ethyl)amine [prepared as described in step (a) above], 2.14 g of nickel chloride hexahydrate and 623 mg of sodium borohydride were reacted, to obtain 1.16 g of the title compound as a yellow oil.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-3707165503f74bae86c7f01b829e8667
Source dataset
uspto-grants-2001_12
Patent number
US06329405B1

Reaction notes

Loading…