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

HRID 2269442Notes

Reaction equation

HRID 2269442 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])[C:14]([O:20][CH3:21])=[C:13]([O:22][CH3:23])[CH:12]=2)=O)=[CH:5][CH:4]=1.Cl.[F:25][C:26]1[CH:27]=[C:28]([CH:33]([NH2:35])[CH3:34])[CH:29]=[CH:30][C:31]=1[F:32].C(N(CC)CC)C.C([BH3-])#N.[Na+]>[Ti](Cl)(Cl)(Cl)Cl.C(O)(=O)C>[F:25][C:26]1[CH:27]=[C:28]([CH:33]([NH:35][CH:9]([C:11]2[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[C:14]([O:20][CH3:21])=[C:13]([O:22][CH3:23])[CH:12]=2)[C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH3:34])[CH:29]=[CH:30][C:31]=1[F:32]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 5003444Sodium cyanoborohydrideHCID 18334221HCID 18334221, compoundHCID 18347113Benzenemethanamine, 3,4-difluoro-α-methyl-, hydrochloride (1:1)

Product 1

HCID 18334197N-[1-(3,4-Difluorophenyl)ethyl]-N-[(3,4-dimethoxy-5-nitrophenyl)-(4-methoxyphenyl)methyl]amineYield 93.9%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 176Acetic AcidSolvent

Procedure

Following a similar procedure to that described in Example (1a), 700 mg of 3,4-dimethoxy-5-nitrophenyl 4-methoxyphenyl ketone, 854 mg of 1-(3,4-difluorophenyl)ethylamine hydrochloride, 1.84 ml of triethylamine, 0.29 ml of titanium tetrachloride, 616 mg of sodium cyanoborohydride and 0.19 ml of acetic acid were reacted, to obtain 950 mg of the title compound as a yellow oil.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-8decf6faa133429cb06d4c5da8fa6cd9
Source dataset
uspto-grants-2001_12
Patent number
US06329405B1

Reaction notes

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