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

HRID 2269410Notes

Reaction equation

HRID 2269410 reaction equation
C1([C:7]2[C:12]([N+:13]([O-])=O)=[CH:11][CH:10]=[CH:9][C:8]=2[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([N+]([O-])=O)[C:19]=2C2CCCCC2)=O)CCCCC1.Cl.[F:34][C:35]1[CH:36]=[C:37]([CH:42]([NH2:44])[CH3:43])[CH:38]=[CH:39][C:40]=1[F:41].[BH4-].[Na+]>[Ti](Cl)(Cl)(Cl)Cl.O.O.O.O.O.O.[Ni](Cl)Cl>[CH:18]1([CH:16]([NH:44][CH:42]([C:37]2[CH:38]=[CH:39][C:40]([F:41])=[C:35]([F:34])[CH:36]=2)[CH3:43])[C:8]2[CH:7]=[C:12]([NH2:13])[CH:11]=[CH:10][CH:9]=2)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1

Participants

6

Reactant 3

HCID 4311764Sodium borohydrideHCID 18347113Benzenemethanamine, 3,4-difluoro-α-methyl-, hydrochloride (1:1)HCID 88201955HCID 88201955, compound

Product 1

HCID 183340853-{Cyclohexyl-[1-(3,4-difluorophenyl)ethylamino]methyl}phenylamineYield 67.2%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 11791229Dichloronickel;hexahydrateCatalyst

Procedure

In a similar manner to that described in Example (25a), cyclohexyl-3-nitrophenylketone (3.0 g), 1-(3,4-difluorophenyl)ethylamine hydrochloride (4.98 g) triethylamine (10.8 ml), titanium tetrachloride (1.70 ml), nickel chloride hexahydrate (6.11 g), and sodium borohydride (2.05 g) were reacted, to afford the title compound (1.59 g) as a yellow oil.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-86a73003309c49208cc8e9076de99398
Source dataset
uspto-grants-2001_12
Patent number
US06329405B1

Reaction notes

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