Triethylamine → N-[1-(3,5-Difluorophenyl)ethyl]-N-[(3-nitrophenyl)-(4-propoxyphenyl)methyl]amine

HRID 2269452Notes

Reaction equation

HRID 2269452 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=2)=O)=[CH:7][CH:6]=1)[CH2:2][CH3:3].[F:22][C:23]1[CH:24]=[C:25]([CH:30]([NH2:32])[CH3:31])[CH:26]=[C:27]([F:29])[CH:28]=1.C(N(CC)CC)C.C([BH3-])#N.[Na+]>[Ti](Cl)(Cl)(Cl)Cl.C(O)(=O)C>[F:22][C:23]1[CH:24]=[C:25]([CH:30]([NH:32][CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=2)[C:8]2[CH:9]=[CH:10][C:5]([O:4][CH2:1][CH2:2][CH3:3])=[CH:6][CH:7]=2)[CH3:31])[CH:26]=[C:27]([F:29])[CH:28]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 2783196(RS)-1-(3,5-Difluorophenyl)ethylamineHCID 5003444Sodium cyanoborohydrideHCID 183470373-Nitrophenyl 4-propoxyphenyl ketone

Product 1

HCID 18334077N-[1-(3,5-Difluorophenyl)ethyl]-N-[(3-nitrophenyl)-(4-propoxyphenyl)methyl]amineYield 98.2%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 176Acetic AcidSolvent

Procedure

Following a similar procedure to that described in Example (1a), 790 mg of 3-nitrophenyl 4-propoxyphenyl ketone, 870 mg of 1-(3,5-difluorophenyl)ethylamine, 1.54 ml of triethylamine, 0.37 ml of titanium tetrachloride, 733 mg of sodium cyanoborohydride and 0.24 ml of acetic acid were reacted, to obtain 1.16 g of the title compound as a yellow oil.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-1201079fca7143758179ab4e2b09d708
Source dataset
uspto-grants-2001_12
Patent number
US06329405B1

Reaction notes

Loading…