Sodium borohydride → 3-{[1-(3,4-Difluorophenyl)ethylamino]-(4-methoxyphenyl)methyl}-4-fluorophenylamine

HRID 2269464Notes

Reaction equation

HRID 2269464 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]([NH:11][CH:12]([C:21]2[CH:26]=[C:25]([N+:27]([O-])=O)[CH:24]=[CH:23][C:22]=2[F:30])[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[CH3:10])[CH:5]=[CH:6][C:7]=1[F:8].[BH4-].[Na+]>O.O.O.O.O.O.[Ni](Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:9]([NH:11][CH:12]([C:13]2[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=2)[C:21]2[CH:26]=[C:25]([NH2:27])[CH:24]=[CH:23][C:22]=2[F:30])[CH3:10])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 18334198N-[1-(3,4-Difluorophenyl)ethyl]-N-[(2-fluoro-5-nitrophenyl)-(4-methoxyphenyl)methyl]amine

Product 1

HCID 183341053-{[1-(3,4-Difluorophenyl)ethylamino]-(4-methoxyphenyl)methyl}-4-fluorophenylamine

Reagents, catalysts & solvents 1

HCID 11791229Dichloronickel;hexahydrateCatalyst

Procedure

Following a reaction and purification procedure similar to those described in Example (59b), 800 mg of N-[1-(3,4-difluorophenyl)ethyl]-N-[(2-fluoro-5-nitrophenyl)-(4-methoxyphenyl)methyl]amine [prepared as described in step (a) above], 1.05 g of nickel chloride hexahydrate and 306 mg of sodium borohydride were reacted, to obtain 330 mg of isomer A and 350 mg of isomer B of the title compound as yellow oils, respectively.

Workup

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

Sources & evidence

ORD record
ord-c5e1fec2f99c481ba2d98339cbfc1a38
Source dataset
uspto-grants-2001_12
Patent number
US06329405B1

Reaction notes

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