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

HRID 2269444Notes

Reaction equation

HRID 2269444 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]=[C:30]([F:32])[CH:31]=1.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]=[C:30]([F:32])[CH:31]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 5003444Sodium cyanoborohydrideHCID 18334221HCID 18334221, compoundHCID 183470361-(3,5-Difluorophenyl)ethanamine hydrochloride

Product 1

HCID 183470481-(3,5-difluorophenyl)ethyl-N-[(3,4-dimethoxy-5-nitrophenyl)-(4-methoxyphenyl)methyl]amineYield 91.4%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 176Acetic AcidSolvent

Procedure

Following a similar procedure to that described in Example (1a), 750 mg of 3,4-dimethoxy-5-nitrophenyl 4-methoxyphenyl ketone, 915 mg of 1-(3,5-difluorophenyl)ethylamine hydrochloride, 1.98 ml of triethylamine, 0.31 ml of titanium tetrachloride, 660 mg of sodium cyanoborohydride and 0.20 ml of acetic acid were reacted, to obtain 990 mg of the title compound as a yellow oil.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-5d6affbdf54448e796c7783a29a4bb76
Source dataset
uspto-grants-2001_12
Patent number
US06329405B1

Reaction notes

Loading…