Methylamine → 2-Chloro-5-[3-(methylamino)propyl]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide, acetate salt
Reaction equation
[CH3:1][NH2:2].[Cl:3][C:4]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26]OS(C)(=O)=O)=[CH:20][C:5]=1[C:6]([NH:8][CH2:9][C:10]12[CH2:19][CH:14]3[CH2:15][CH:16]([CH2:18][CH:12]([CH2:13]3)[CH2:11]1)[CH2:17]2)=[O:7].[C:32]([O:35]CC)(=[O:34])[CH3:33]>>[C:32]([OH:35])(=[O:34])[CH3:33].[Cl:3][C:4]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][NH:2][CH3:1])=[CH:20][C:5]=1[C:6]([NH:8][CH2:9][C:10]12[CH2:19][CH:14]3[CH2:13][CH:12]([CH2:18][CH:16]([CH2:15]3)[CH2:17]1)[CH2:11]2)=[O:7]Participants
4
Conditions
- Temperature
- 70 °C
Procedure
Methylamine (2 M tetrahydrofuran, 8 ml) was added to 2-chloro-5-[3-[(methylsulfonyl)oxy]propyl]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (0.250 g, Example 6e) and heated in a sealed tube at 70° C. for 18 h. On cooling to ambient temperature, the solution was diluted with ethyl acetate and extracted twice with saturated sodium hydrogencarbonate solution and once with brine, dried over magnesium sulfate and concentrated under reduced pressure. Purification by preperative reverse phase HPLC (eluting with a gradient of acetonitrile in 0.1% aqueous ammonium acetate/25-95%) gave the title compound as the acetate salt (0.140 g).