Methanol → (S)-(+)-N-methyl-3-methyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine

HRID 1915187Notes

Reaction equation

HRID 1915187 reaction equation
[CH3:1][N:2]([CH2:5][CH2:6][CH:7]([O:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1)[C:8]1[S:9][CH:10]=[CH:11][CH:12]=1)OC.[CH3:24]O>[Ni]>[CH3:1][NH:2][CH2:5][CH2:6][C@:7]([CH3:24])([O:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1)[C:8]1[S:9][CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 46913234N-methyl-N-methoxyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine

Product 1

HCID 42598152(S)-(+)-N-methyl-3-methyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

N-methyl-N-methoxyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine obtained in example 3 was dissolved in 15 mL of methanol with 0.67 g of Raney-nickel charged in a glass autoclave. The resulting solution was hydrogenated at 50□ for 12 hours. Upon completion of hydrogenation, the reaction mixture was filtered and solvent is removed under reduced pressure, and then the desired compound is obtained as an oily compound (12.0 g, 96.4% by HPLC assay). 1H NMR (400 MHz, CDCl3) δ (ppm)=2.2 (m, 1H), 2.4 (m, 1H), 2.4 (s, 3H), 2.8 (m, 2H), 5.8 (m, 1H), 6.8 (d, 1H), 6.9 (m, 1H), 7.1 (d, 1H), 7.2 (d, 1H), 7.3 (d, 1H), 7.4 (m, 1H), 7.5 (m, 2H), 7.8 (m, 1H), 8.3 (m, 1H).

Workup

  1. additioncharged in a glass autoclave
  2. filtrationUpon completion of hydrogenation, the reaction mixture was filtered
  3. customsolvent is removed under reduced pressure

Sources & evidence

ORD record
ord-b0d3827bacbe42e99a6db93b2557681c
Source dataset
uspto-grants-2013_12
Patent number
US08614336B2

Reaction notes

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