Triethylamine → N-[(3-Nitrophenyl)-(4-fluorophenyl)methyl]-N-[1-(3,4-difluorophenyl)ethyl]amine

HRID 2269402Notes

Reaction equation

HRID 2269402 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-:16])=[O:15])[CH:9]=2)=O)=[CH:4][CH:3]=1.Cl.[F:20][C:21]1[CH:22]=[C:23]([CH:28]([NH2:30])[CH3:29])[CH:24]=[CH:25][C:26]=1[F:27].C(N(CC)CC)C.C([BH3-])#N.[Na+]>[Ti](Cl)(Cl)(Cl)Cl.C(O)(=O)C>[N+:14]([C:10]1[CH:9]=[C:8]([CH:6]([C:5]2[CH:17]=[CH:18][C:2]([F:1])=[CH:3][CH:4]=2)[NH:30][CH:28]([C:23]2[CH:24]=[CH:25][C:26]([F:27])=[C:21]([F:20])[CH:22]=2)[CH3:29])[CH:13]=[CH:12][CH:11]=1)([O-:16])=[O:15]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 5003444Sodium cyanoborohydrideHCID 104905584-Fluoro-3'-nitrobenzophenoneHCID 18347113Benzenemethanamine, 3,4-difluoro-α-methyl-, hydrochloride (1:1)

Product 1

HCID 18334151N-[(3-Nitrophenyl)-(4-fluorophenyl)methyl]-N-[1-(3,4-difluorophenyl)ethyl]amineYield 96.1%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 176Acetic AcidSolvent

Procedure

In a similar manner to that described in Example (1a), 4-fluoro-3′-nitrobenzophenone (2.0 g), 1-(3,4-difluorophenyl)ethylamine hydrochloride (3.16 g), triethylamine (6.82 ml), titanium tetrachloride (1.08 ml), sodium cyanoborohydride (2.28 g) and acetic acid (0.7 ml) were reacted, to afford the title compound (3.03 g) as a yellow oil.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-53fc852bbba2495287c85e1e8c4d1ed3
Source dataset
uspto-grants-2001_12
Patent number
US06329405B1

Reaction notes

Loading…