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

HRID 2269461Notes

Reaction equation

HRID 2269461 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[C:13]([N+:18]([O-:20])=[O:19])[CH:12]=2)=O)=[CH:5][CH:4]=1.Cl.[F:22][C:23]1[CH:24]=[C:25]([CH:30]([NH2:32])[CH3:31])[CH:26]=[CH:27][C:28]=1[F:29].C(N(CC)CC)C.C([BH3-])#N.[Na+]>[Ti](Cl)(Cl)(Cl)Cl.C(O)(=O)C>[F:22][C:23]1[CH:24]=[C:25]([CH:30]([NH:32][CH:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[C:13]([N+:18]([O-:20])=[O:19])[CH:12]=2)[C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH3:31])[CH:26]=[CH:27][C:28]=1[F:29]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 5003444Sodium cyanoborohydrideHCID 183342744-Fluoro-3-nitrophenyl 4-methoxyphenyl ketoneHCID 18347113Benzenemethanamine, 3,4-difluoro-α-methyl-, hydrochloride (1:1)

Product 1

HCID 18347053N-[1-(3,4-Difluorophenyl)ethyl]-N-[(4-fluoro-3-nitrophenyl)-(4-methoxyphenyl)methyl}amineYield 86.9%

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-fluoro-3-nitrophenyl 4-methoxyphenyl ketone, 2.81 g of 1-(3,4-difluorophenyl)ethylamine hydrochloride, 6.08 ml of triethylamine, 0.96 ml of titanium tetrachloride, 2.03 g of sodium cyanoborohydride and 0.62 ml of acetic acid were reacted, to obtain 2.63 g of the title compound as a yellow oil.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-659fbc404ecb4b0c800e3c561479bd55
Source dataset
uspto-grants-2001_12
Patent number
US06329405B1

Reaction notes

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