Sodium borohydride → 5-{[1-(3,5-Difluorophenyl)ethylamino]-(4-methoxyphenyl)methyl}-2,3-dimethoxyphenylamine

HRID 2269445Notes

Reaction equation

HRID 2269445 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)[C:24]([O:30][CH3:31])=[C:23]([O:32][CH3:33])[CH:22]=2)[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[CH3:10])[CH:5]=[C:6]([F:8])[CH:7]=1.[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:22]=[C:23]([O:32][CH3:33])[C:24]([O:30][CH3:31])=[C:25]([NH2:27])[CH:26]=2)[CH3:10])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 183470481-(3,5-difluorophenyl)ethyl-N-[(3,4-dimethoxy-5-nitrophenyl)-(4-methoxyphenyl)methyl]amine

Product 1

HCID 183471125-{[1-(3,5-Difluorophenyl)ethylamino]-(4-methoxyphenyl)methyl}-2,3-dimethoxyphenylamine

Reagents, catalysts & solvents 1

HCID 11791229Dichloronickel;hexahydrateCatalyst

Procedure

Following a similar procedure to that described in Example (1b), 870 mg of N-[1-(3,5-difluorophenyl)ethyl-N-[(3,4-dimethoxy-5-nitrophenyl)-(4-methoxyphenyl)methyl]amine [prepared as described in step (a) above], 1.04 g of nickel chloride hexahydrate and 302 mg of sodium borohydride were reacted, to obtain 550 mg of the title compound as a colorless oil.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-c02772584edb4d33a5803456d7d51b12
Source dataset
uspto-grants-2001_12
Patent number
US06329405B1

Reaction notes

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