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

HRID 2269450Notes

Reaction equation

HRID 2269450 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH3:20])=[CH:14][CH:13]=2)=O)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[F:21][C:22]1[CH:23]=[C:24]([CH:29]([NH2:31])[CH3:30])[CH:25]=[C:26]([F:28])[CH:27]=1.C(N(CC)CC)C.C([BH3-])#N.[Na+]>[Ti](Cl)(Cl)(Cl)Cl.C(O)(=O)C>[F:21][C:22]1[CH:23]=[C:24]([CH:29]([NH:31][CH:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH3:20])=[CH:14][CH:13]=2)[C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[CH3:30])[CH:25]=[C:26]([F:28])[CH:27]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 868593(4-Ethoxyphenyl)(3-nitrophenyl)methanoneHCID 2783196(RS)-1-(3,5-Difluorophenyl)ethylamineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 18334176N-[1-(3,5-Difluorophenyl)ethyl]-N-[(4-ethoxyphenyl)-(3-nitrophenyl)methyl]amineYield 92.7%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 176Acetic AcidSolvent

Procedure

Following a similar procedure to that described in Example (1a), 1.0 g of 4-ethoxyphenyl 3-nitrophenyl ketone, 1.16 g of 1-(3,5-difluorophenyl)ethylamine, 2.01 ml of triethylamine, 0.49 ml of titanium tetrachloride, 975 mg of sodium cyanoborohydride and 0.32 ml of acetic acid were reacted, to obtain 1.41 g of the title compound as a yellow oil.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-ee7b100cb7f5415887b2980a55be218c
Source dataset
uspto-grants-2001_12
Patent number
US06329405B1

Reaction notes

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