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

HRID 2269456Notes

Reaction equation

HRID 2269456 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=O)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].Cl.[F:20][C:21]1[CH:22]=[C:23]([C@H:28]([NH2:30])[CH3:29])[CH:24]=[C:25]([F:27])[CH:26]=1.C(N(CC)CC)C.C([BH3-])#N.[Na+]>[Ti](Cl)(Cl)(Cl)Cl.C(O)(=O)C>[F:20][C:21]1[CH:22]=[C:23]([C@H:28]([NH:30][CH:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[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)[CH3:29])[CH:24]=[C:25]([F:27])[CH:26]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 5003444Sodium cyanoborohydrideHCID 104905584-Fluoro-3'-nitrobenzophenoneHCID 44828509(1R)-1-(3,5-difluorophenyl)ethan-1-amine hydrochloride

Product 1

HCID 70189758N-[(R)-1-(3,5-Difluorophenyl)ethyl]-N-[(4-fluorophenyl)-(3-nitrophenyl)methyl]amineYield 94.8%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 176Acetic AcidSolvent

Procedure

Following a similar procedure to that described in Example (1a), 3.0 g of 4-fluorophenyl 3-nitrophenyl ketone, 3.55 g of (R)-1-(3,5-difluorophenyl)ethylamine hydrochloride, 9.38 ml of triethylamine, 1.61 ml of titanium tetrachloride, 3.08 g of sodium cyanoborohydride and 1.05 ml of acetic acid were reacted, to obtain 4.48 g of the title compound as a yellow oil.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-bf6e55dcd2a64ce0b31df44de89a0a4d
Source dataset
uspto-grants-2001_12
Patent number
US06329405B1

Reaction notes

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