alpha-(3,4-Dimethoxyphenyl)benzeneethanamine → (R)-N-[1-(3,4-Dimethoxyphenyl)-2-phenylethyl]-2-hydroxy-2-(2-chloropyrid-5-yl)-ethylamine

HRID 861441Notes

Reaction equation

HRID 861441 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

Reactant 2

HCID 411116alpha-(3,4-Dimethoxyphenyl)benzeneethanamineHCID 545744082-Chloro-5-[(2R)-oxiran-2-yl]pyridine

Product 1

HCID 86752026(R)-N-[1-(3,4-Dimethoxyphenyl)-2-phenylethyl]-2-hydroxy-2-(2-chloropyrid-5-yl)-ethylamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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).

Workup

  1. temperatureat reflux in an oil bath overnight
  2. customThe yellow residue was purified by flash chromatography on silica gel (eluent: ethylacetate: hexanes:9:1)

Sources & evidence

ORD record
ord-1f70e61c1ca04e88b25d6bbb76c8efbc
Source dataset
uspto-grants-1998_02
Patent number
US05714506

Reaction notes

Loading…