Tert-butyl 3-(3-chlorophenyl)-3-(3-methoxypropoxy)propyl(isopropyl)carbamate → 3-(3-chlorophenyl)-N-isopropyl-3-(3-methoxypropoxy)propan-1-amine
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([O:22][CH2:23][CH2:24][CH2:25][O:26][CH3:27])[CH2:9][CH2:10][N:11]([CH:19]([CH3:21])[CH3:20])C(=O)OC(C)(C)C)[CH:5]=[CH:6][CH:7]=1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([O:22][CH2:23][CH2:24][CH2:25][O:26][CH3:27])[CH2:9][CH2:10][NH:11][CH:19]([CH3:20])[CH3:21])[CH:5]=[CH:6][CH:7]=1Participants
3
Procedure
tert-butyl 3-(3-chlorophenyl)-3-(3-methoxypropoxy)propyl(isopropyl)carbamate was dissolved in a solution of 20% (V/V) TFA/CH2Cl2 (10 mL) and allowed to stir for 1 hour. The solvent and reagent were evaporated before re-dissolving in CH2Cl2 and washing with NaHCO3 saturated solution. The crude 3-(3-chlorophenyl)-N-isopropyl-3-(3-methoxypropoxy)propan-1-amine was isolated (138 mg) and used as is. MS ESI+ve m/z 299 (M+).