Hydrochloric Acid → 1-(4-(Azetidin-3-yloxy)-2-methylphenyl)-N,N-dimethylmethanamine
Reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:22]=[CH:21][C:8]([O:9][CH:10]2[CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11]2)=[CH:7][C:6]=1[CH3:23])[CH3:3].Cl>CO>[NH:12]1[CH2:11][CH:10]([O:9][C:8]2[CH:21]=[CH:22][C:5]([CH2:4][N:2]([CH3:3])[CH3:1])=[C:6]([CH3:23])[CH:7]=2)[CH2:13]1Participants
4
Procedure
Intermediate 20B (3.1 g, 9.7 mmol) was dissolved in MeOH (10 mL) and HCl in MeOH (1.25 M, 50 mL) was added. The reaction mixture was stirred at RT overnight. The mixture was concentrated, the residue was dissolved in water (15 mL) and DCM (100 mL) was added. While stirring an aqueous solution of K2CO3 (sat., 30 mL) was added and the two phases were separated through a phase separator. The solvent was removed by evaporation. There was obtained 1.96 g (92%) of 20C as a colorless oil. 1H NMR (600 MHz, CDCl3): δ 2.21 (s, 6H), 2.32 (s, 3H), 3.29 (s, 2H), 3.71-3.83 (m, 2H), 3.84-3.95 (m, 2H), 4.92-5.02 (m, 1H), 6.51 (d, 1H), 6.57 (s, 1H), 7.10 (d, 1H).