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

HRID 2269459Notes

Reaction equation

HRID 2269459 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=O)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[F:19][C:20]1[CH:21]=[C:22]([CH:27]([NH2:29])[CH3:28])[CH:23]=[C:24]([F:26])[CH:25]=1.C(N(CC)CC)C.C([BH3-])#N.[Na+]>[Ti](Cl)(Cl)(Cl)Cl.C(O)(=O)C>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([CH:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[NH:29][CH:27]([C:22]2[CH:23]=[C:24]([F:26])[CH:25]=[C:20]([F:19])[CH:21]=2)[CH3:28])=[CH:13][CH:14]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 7673464-Chloro-3'-nitrobenzophenoneHCID 2783196(RS)-1-(3,5-Difluorophenyl)ethylamineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 18334265N-[(4-Chlorophenyl)-(3-nitrophenyl)methyl]-N-[1-(3,5-difluorophenyl)ethyl]amineYield 94.8%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 176Acetic AcidSolvent

Procedure

Following a similar procedure to that described in Example (1a), 2.0 g of 4-chlorophenyl 3-nitrophenyl ketone, 2.40 g of 1-(3,5-difluorophenyl)ethylamine, 4.26 ml of triethylamine, 1.01 ml of titanium tetrachloride, 3.02 g of sodium cyanoborohydride and 0.66 ml of acetic acid were reacted, to obtain 2.92 g of the title compound as a yellow oil.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-2d4ad6ce739842339aa64a47cff038d9
Source dataset
uspto-grants-2001_12
Patent number
US06329405B1

Reaction notes

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