Acetyl chloride → HCID 70624671, compound

Reaction equation

[C:1](Cl)(=[O:3])[CH3:2].[CH3:5][O:6][C:7]1[CH:8]=[C:9]([C@H:15]2[C@@H:20]([OH:21])[CH2:19][CH2:18][CH2:17][NH:16]2)[CH:10]=[CH:11][C:12]=1[O:13][CH3:14]>C(Cl)Cl.[OH-].[Na+]>[C:1]([N:16]1[CH2:17][CH2:18][CH2:19][C@H:20]([OH:21])[C@@H:15]1[C:9]1[CH:10]=[CH:11][C:12]([O:13][CH3:14])=[C:7]([O:6][CH3:5])[CH:8]=1)(=[O:3])[CH3:2]

Participants

Procedure

Acetyl chloride (9.75 g, 125 mmoles) is added dropwise to a cooled (0° to 10° C) and stirred solution of cis-2-(3,4-dimethoxyphenyl)-3-piperidinol (25.0 g, 105 mmoles, described in Example 4) in methylene chloride (200 ml) and 8N sodium hydroxide (100 ml). The mixture is stirred for 30 minutes and the organic phase is separated. The aqueous phase is extracted with methylene chloride. The organic extracts are washed with dilute hydrochloric acid, aqueous sodium carbonate, brine, dried (MgSO4) and evaporated. The residue is subjected to chromatography on silica gel using methanol-ether 1:3 and the eluates are evaporated to give cis-1-acetyl-2-(3,4-dimethoxyphenyl)-3-piperidinol; nmr (CDCl3) δ 2.12 (s, 3H), 3.86 (s, 6H) and 7.0 (m, 3H).