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

HRID 2269447Notes

Reaction equation

HRID 2269447 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[O:30][CH3:31])[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:26]=[C:25]([NH2:27])[CH:24]=[CH:23][C:22]=2[O:30][CH3:31])[CH3:10])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 18334175N-[1-(3,5-Difluorophenyl)ethyl]-N-[(2-methoxy-5-nitrophenyl)-(4-methoxyphenyl)methyl]amine

Product 1

HCID 183342433-{[1-(3,5-Difluorophenyl)ethylamino]-(4-methoxyphenyl)methyl}-4-methoxyphenylamine

Reagents, catalysts & solvents 1

HCID 11791229Dichloronickel;hexahydrateCatalyst

Procedure

Following a reaction and purification procedure similar to those described in Example (59b), 1.75 g of N-[1-(3,5-difluorophenyl)ethyl]-N-[(2-methoxy-5-nitrophenyl)-(4-methoxyphenyl)methyl]amine [prepared as described in step (a) above], 2.24 g of nickel chloride hexahydrate and 651 mg of sodium borohydride were reacted, to obtain 471 mg of isomer A and 650 mg of isomer B of the title compound were obtained as a yellow oil and an orange solid, respectively.

Workup

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

Sources & evidence

ORD record
ord-32aafad258e646bfb7c9aa5ee279e138
Source dataset
uspto-grants-2001_12
Patent number
US06329405B1

Reaction notes

Loading…