Diketene → 3-(4,4-Diphenylpiperid-1-yl)-propyl acetoacetate

Reaction equation

[C:1]1([C:7]2([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][CH2:15][OH:16])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:23]=[C:24]1[O:28][C:26](=[O:27])[CH2:25]1>C1(C)C=CC=CC=1.CC(C)=O>[C:26]([O:16][CH2:15][CH2:14][CH2:13][N:10]1[CH2:9][CH2:8][C:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:12][CH2:11]1)(=[O:27])[CH2:25][C:24]([CH3:23])=[O:28]

Participants

Procedure

23.6 g of 3-(4,4-diphenylpiperid-1-yl)-propanol are dissolved in 100 ml of absolute toluene, and 16 ml of a 50% strength solution of diketene in acetone are added, with stirring. After the mixture has been left to stand at room temperature for several days (control by thin layer chromatography), it is concentrated, and the residue is dried under a high vacuum. The pale yellow viscous oil which remains is employed for the next stage without further purification.