alpha-(3,4-Dimethoxyphenyl)benzeneethanamine → (R)-N-[1-(3,4-Dimethoxyphenyl)-2-phenylethyl]-2-hydroxy-2-(2-chloropyrid-5-yl)-ethylamine
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([NH2:19])[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([C@@H:27]2[CH2:29][O:28]2)=[CH:23][N:22]=1>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([NH:19][CH2:29][C@H:27]([OH:28])[C:24]2[CH:25]=[CH:26][C:21]([Cl:20])=[N:22][CH:23]=2)[CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]Participants
4
Procedure
A solution of α-(3.4-dimethoxyphenyl)benzeneethanamine (257 mg, 1 mmol, 2 eq) and (R)-(2-chloropyrid-5-yl)oxirane (Example 3, 77 mg, 0.5 mmol) in dry methanol in a gas tight vessel was heated at reflux in an oil bath overnight. The reaction was cooled to room temperature and then the solvent was stripped under vacuum. The yellow residue was purified by flash chromatography on silica gel (eluent: ethylacetate: hexanes:9:1) to give the adduct as a white solid. 1H NMR (400 MHz, CDCl3)δ 8.20 (m, 1H), 7.53 (m, 1H), 7.07-7.30 (m, 6H), 6.71-6.8 (m, 3H), 4.38-4.58 (m, 1H), 3.87 and 3.86 (s, 3H. OCH3), 3.82 (s, 3H, OCH3), 3.70-3.85 (m, 1H), 2.80-3.0 (m, 2H), 2,64-2.73 (m, 1H), 2.35-2.51 (m, 1H).