Ammonium Chloride → HCID 131723678, compound

Reaction equation

[N+:1]([C:4]1[CH:23]=[CH:22][CH:21]=[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])([O-])=O.[Cl-:24].[NH4+:25]>[Fe].C(O)C.O>[ClH:24].[ClH:24].[NH2:1][C:4]1[C:23]([N:25]2[CH2:10][CH2:9][NH:8][CH2:6][CH2:5]2)=[CH:22][CH:21]=[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]

Participants

Procedure

A suspension of 3-(4-{1,1-dimethylethyl}oxycarbonyl]-piperazin-1-yl)-2-nitro-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (3.8 g, Example 1b), iron powder (2.13 g) and ammonium chloride (2.04 g) in 2:1 ethanol/water (90 ml) was heated at reflux, under a nitrogen atmosphere, for 2 h. The cooled reaction mixture was filtered and the filtrate partitioned between water and ethyl acetate. The organic layer was separated and washed with water twice further, dried over magnesium sulfate, filtered and the filtrate concentrated under reduced pressure to give a residue. Purification of the residue by chromatography over silica gel, eluting with 20% ethyl acetate in iso-hexane, yielded the subtitle compound as a solid (2.27 g).