4-Methoxybenzoyl isocyanate → HCID 12608517, compound

Reaction equation

[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH:9]([CH:11]2[O:16][C:15]3[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=3[O:13][CH2:12]2)[OH:10])[CH2:4][CH2:3]1.[CH3:21][O:22][C:23]1[CH:33]=[CH:32][C:26]([C:27]([N:29]=[C:30]=[O:31])=[O:28])=[CH:25][CH:24]=1>[Na].C1C=CC=CC=1>[CH3:21][O:22][C:23]1[CH:33]=[CH:32][C:26]([C:27]([NH:29][C:30]([NH:1][CH:2]2[CH2:7][CH2:6][N:5]([CH2:8][CH:9]([CH:11]3[O:16][C:15]4[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=4[O:13][CH2:12]3)[OH:10])[CH2:4][CH2:3]2)=[O:31])=[O:28])=[CH:25][CH:24]=1

Participants

Procedure

Erythro 4-amino-1-[2-(1,4-benzodioxan-2-yl)-2-hydroxy-ethyl]piperidine (2.0 g 0.0072 m)) was dissolved in sodium dried benzene (100 mls). To the stirring solution was added p-methoxy benzoyl isocyanate (1.27 g 0.0072m) in benzene (20 mls) and the solution stirred at room temperature for 18 hours. The solvent was evaporated and the residue heated with isopropyl alcohol. The insoluble solid was filtered off and triturated with hot ethanol, filtered and dried to give the title compound (0.5 g 15%).