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

HRID 2269448Notes

Reaction equation

HRID 2269448 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=O)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].Cl.[F:21][C:22]1[CH:23]=[C:24]([C@H: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]([C@H:29]([NH:31][CH:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[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 794540(4-Methoxyphenyl)(3-nitrophenyl)methanoneHCID 5003444Sodium cyanoborohydrideHCID 44828509(1R)-1-(3,5-difluorophenyl)ethan-1-amine hydrochloride

Product 1

HCID 70189169N-[(R)-1-(3,5-Difluorophenyl)ethyl]-N-[(4-methoxyphenyl)-(3-nitrophenyl)methyl]amine

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 176Acetic AcidSolvent

Procedure

Following a reaction and purification procedure similar to those described in Example (1a), 4.42 of 4-methoxyphenyl 3-nitrophenyl ketone, 4.42 g of (R)-1-(3,5-difluorophenyl)ethylamine hydrochloride, 11.7 ml of triethylamine, 2.01 ml of titanium tetrachloride, 4.25 g of sodium cyanoborohydride and 1.31 ml of acetic acid were reacted, to obtain 860 mg of the more polar isomer B of the title compound as a yellow oil.

Workup

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Sources & evidence

ORD record
ord-19a5e6c2483d4f36aba018bc6e95db09
Source dataset
uspto-grants-2001_12
Patent number
US06329405B1

Reaction notes

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