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

HRID 2269443Notes

Reaction equation

HRID 2269443 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]=[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:22]=[C:23]([O:32][CH3:33])[C:24]([O:30][CH3:31])=[C:25]([NH2:27])[CH:26]=2)[CH3:10])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 18334197N-[1-(3,4-Difluorophenyl)ethyl]-N-[(3,4-dimethoxy-5-nitrophenyl)-(4-methoxyphenyl)methyl]amine

Product 1

HCID 183470295-{[1-(3,4-Difluorophenyl)ethylamino]-(4-methoxyphenyl)methyl}-2,3-dimethoxyphenylamineYield 41.7%

Reagents, catalysts & solvents 1

HCID 11791229Dichloronickel;hexahydrateCatalyst

Procedure

Following a reaction and purification procedure similar to those described in Example (1b), 950 mg of N-[1-(3,4-difluorophenyl)ethyl]-N-[(3,4-dimethoxy-5-nitrophenyl)-(4-methoxyphenyl)methyl]amine [prepared as described in step (a) above], 985 mg of nickel chloride hexahydrate and 330 mg of sodium borohydride were reacted. The crude product was purified by chromatography through a silica gel column using a 10:1 by volume mixture of toluene and ethyl acetate as eluant, to afford isomer A of the title compound (215 mg) as a yellow oil and isomer B of the title compound (370 mg) as a yellow oil, respectively.

Workup

  1. customa reaction and purification procedure similar to
  2. customwere reacted
  3. customThe crude product was purified by chromatography through a silica gel column
  4. additionby volume mixture of toluene and ethyl acetate as eluant

Sources & evidence

ORD record
ord-2e00eb5ab5b446de93335ea89cb3e403
Source dataset
uspto-grants-2001_12
Patent number
US06329405B1

Reaction notes

Loading…