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

HRID 2269468Notes

Reaction equation

HRID 2269468 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=O)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].Cl.[CH3:21][C:22]1[CH:23]=[C:24]([CH:29]([NH2:31])[CH3:30])[CH:25]=[CH:26][C:27]=1[CH3:28].C(N(CC)CC)C.C([BH3-])#N.[Na+]>[Ti](Cl)(Cl)(Cl)Cl.C(O)(=O)C>[CH3:21][C:22]1[CH:23]=[C:24]([CH:29]([NH:31][CH:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[CH3:30])[CH:25]=[CH:26][C:27]=1[CH3:28]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 794540(4-Methoxyphenyl)(3-nitrophenyl)methanoneHCID 5003444Sodium cyanoborohydrideHCID 183471231-(3,4-Dimethylphenyl)ethan-1-amine hydrochloride

Product 1

HCID 18347035N-[1-(3,4-Dimethylphenyl)ethyl]-N-[(4-methoxyphenyl)-(3-nitrophenyl)methyl]amineYield 95.5%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 176Acetic AcidSolvent

Procedure

Following a similar procedure to that described in Example (1a), 1.0 g of 4-methoxyphenyl 3-nitrophenyl ketone, 1.44 g of 1-(3,4-dimethylphenyl)ethylamine hydrochloride, 3.25 ml of triethylamine, 0.51 ml of titanium tetrachloride, 1.03 g of sodium cyanoborohydride and 0.33 ml of acetic acid were reacted, to obtain 1.45 g of the title compound as a yellow oil.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-12901b3dc33741d69dae9db3d1b7ff69
Source dataset
uspto-grants-2001_12
Patent number
US06329405B1

Reaction notes

Loading…