Triethylamine → N-[1-(3,5-Difluorophenyl)ethyl]-N-[(2-methoxy-5-nitrophenyl)-(4-methoxyphenyl)methyl]amine

HRID 2269446Notes

Reaction equation

HRID 2269446 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]2[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[CH:13][C:12]=2[O:20][CH3:21])=O)=[CH:5][CH:4]=1.Cl.[F:23][C:24]1[CH:25]=[C:26]([CH:31]([NH2:33])[CH3:32])[CH:27]=[C:28]([F:30])[CH:29]=1.C(N(CC)CC)C.C([BH3-])#N.[Na+]>[Ti](Cl)(Cl)(Cl)Cl.C(O)(=O)C>[F:23][C:24]1[CH:25]=[C:26]([CH:31]([NH:33][CH:9]([C:11]2[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[CH:13][C:12]=2[O:20][CH3:21])[C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH3:32])[CH:27]=[C:28]([F:30])[CH:29]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 5003444Sodium cyanoborohydrideHCID 183470361-(3,5-Difluorophenyl)ethanamine hydrochlorideHCID 701880992-Methoxy-5-nitrophenyl 4-methoxyphenyl ketone

Product 1

HCID 18334175N-[1-(3,5-Difluorophenyl)ethyl]-N-[(2-methoxy-5-nitrophenyl)-(4-methoxyphenyl)methyl]amineYield 92.5%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 176Acetic AcidSolvent

Procedure

Following a similar procedure to that described in Example (1a), 1.29 g of 2-methoxy-5-nitrophenyl 4-methoxyphenyl ketone, 1.74 g of 1-(3,5-difluorophenyl)ethylamine hydrochloride, 3.76 ml of triethylamine, 0.59 ml of titanium tetrachloride, 1.25 g of sodium cyanoborohydride and 0.39 ml of acetic acid were reacted, to obtain 1.78 g of the title compound as a yellow oil.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-685fbfe573054e3686416645261f8aa9
Source dataset
uspto-grants-2001_12
Patent number
US06329405B1

Reaction notes

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