2-Bromopropane → 1-Isopropyl-4-(4-nitrophenoxy)-4-phenylpiperidine

Reaction equation

[N+:1]([C:4]1[CH:22]=[CH:21][C:7]([O:8][C:9]2([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[CH:29](Br)([CH3:31])[CH3:30]>CC(CC)=O>[CH:29]([N:12]1[CH2:11][CH2:10][C:9]([O:8][C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:22][CH:21]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:14][CH2:13]1)([CH3:31])[CH3:30]

Participants

Procedure

6.0 g of 4-(4-nitrophenoxy)-4-phenylpiperidine, 2.8 g of potassium carbonate and 3.0 g of isopropyl bromide are boiled under reflux in 50 ml of ethyl methyl ketone for 24 hours. The solvent is evaporated off, the residue is taken up in 100 ml of water, and the aqueous mixture is extracted with 100 ml of diethyl ether. The organic phase is dried over sodium sulfate, filtered over active charcoal and concentrated. 5.2 g of the title compound remain as a viscous, pale yellow oil.