Dichloromethane → 3-{4-[4-(aminodimethylcarbamoylmethyl)-phenoxy]-phenyl}-N,N-dimethylpropionamide hydrochloric acid salt
Reaction equation
C(OC(=O)[NH:7][CH:8]([C:29](=[O:33])[N:30]([CH3:32])[CH3:31])[C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24](=[O:28])[N:25]([CH3:27])[CH3:26])=[CH:18][CH:17]=2)=[CH:11][CH:10]=1)(C)(C)C.C(Cl)[Cl:36]>>[ClH:36].[NH2:7][CH:8]([C:29](=[O:33])[N:30]([CH3:31])[CH3:32])[C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[CH:17]=[CH:18][C:19]([CH2:22][CH2:23][C:24]([N:25]([CH3:26])[CH3:27])=[O:28])=[CH:20][CH:21]=2)=[CH:11][CH:10]=1Participants
3
Conditions
- Temperature
- 2.5 °C
Procedure
The amide compound 40 (0.6 g) was dissolved in CH2Cl2 (30 mL) and cooled to 0-5° C. Hydrogen chloride gas was bubbled through this solution for 20 min. The bubbling was discontinued and the reaction mixture was stirred at room temp for 1 h. The excess HCl was degassed and the CH2Cl2 was removed. The residual solid was triturated with EtOAc (2×50 mL), decanted, and dried to yield the desired compound 41 as a white amorphous solid that was extremely hygroscopic (0.43 g, 83%). 1H NMR (400 MHz, DMSO-d6): 7.46 (d, J=8.8 Hz, 2H), 7.29 (d, J=8.8 Hz, 2H), 7.03 (d, J=8.4 Hz, 2H), 6.95 (d, J=8.4 Hz, 2H), 5.48 (d, J=5.2 Hz, 1H), 2.93 (s, 3H), 2.89 (s, 3H), 2.82 (s, 3H), 2.81 (s, 3H), 2.80 (t, J=8.0 Hz, 2H), 2.59 (t, J=8.0 Hz, 2H). LCMS (m/e): Obsd. 469, Calcd. 369.46.