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

HRID 2269438Notes

Reaction equation

HRID 2269438 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([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:6]=[CH:7][CH:8]=1.Cl.[F:23][C:24]1[CH:25]=[C:26]([CH:31]([NH2:33])[CH3:32])[CH:27]=[CH:28][C:29]=1[F:30].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:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH3:32])[CH:27]=[CH:28][C:29]=1[F:30]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 5003444Sodium cyanoborohydrideHCID 18347113Benzenemethanamine, 3,4-difluoro-α-methyl-, hydrochloride (1:1)HCID 701892132-Methoxy-5-nitrophenyl 3-methoxyphenyl ketone

Product 1

HCID 18334104N-[1-(3,4-Difluorophenyl)ethyl]-N-[(2-methoxy-5-nitrophenyl)-(3-methoxyphenyl)methyl]amineYield 92.8%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 176Acetic AcidSolvent

Procedure

Following a similar procedure to that described in Example (1a), 600 mg of 2-methoxy-5-nitrophenyl 3-methoxyphenyl ketone, 809 mg of 1-(3,4-difluorophenyl)ethylamine hydrochloride, 1.75 ml of triethylamine, 0.28 ml of titanium tetrachloride, 583 mg of sodium cyanoborohydride and 0.18 ml of acetic acid were reacted, to obtain 830 mg of the title compound as a yellow foamy solid.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-edc6aec86af149528e2a0491c8b65974
Source dataset
uspto-grants-2001_12
Patent number
US06329405B1

Reaction notes

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