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

HRID 2269403Notes

Reaction equation

HRID 2269403 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[NH:11][CH:12]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[C:16]([F:21])[CH:15]=2)[CH3:13])[CH:7]=[CH:8][CH:9]=1)([O-])=O.[BH4-].[Na+]>CO.O.O.O.O.O.O.[Ni](Cl)Cl>[F:28][C:25]1[CH:24]=[CH:23][C:22]([CH:10]([NH:11][CH:12]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[C:16]([F:21])[CH:15]=2)[CH3:13])[C:6]2[CH:5]=[C:4]([NH2:1])[CH:9]=[CH:8][CH:7]=2)=[CH:27][CH:26]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 18334151N-[(3-Nitrophenyl)-(4-fluorophenyl)methyl]-N-[1-(3,4-difluorophenyl)ethyl]amine

Product 1

HCID 183341333-{(4-Fluorophenyl)-[1-(3,4-difluorophenyl)ethylamino]methyl}phenylamineYield 21%

Reagents, catalysts & solvents 2

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 887MethanolSolvent

Procedure

In a similar manner to that described in Example (15b), a solution of N-[(3-nitrophenyl)-(4-fluorophenyl)methyl]-N-[1-(3,4-difluorophenyl)ethyl]amine (3.0 g) [prepared as described in step (a) above] in methanol (10 ml), nickel chloride hexahydrate (3.69 g) and sodium borohydride (1.24 g) were reacted, and the reaction mixture was purified to afford isomer A of the title compound (630 mg) as a pale yellow oil and isomer B of the title compound (580 mg) as a pale yellow oil.

Workup

  1. customthe reaction mixture was purified

Sources & evidence

ORD record
ord-45d96bbef1f64f888a119509ab1d9799
Source dataset
uspto-grants-2001_12
Patent number
US06329405B1

Reaction notes

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