Isopropyl iodide → 1,1-Dimethylethyl 4-{[1-(1-methylethyl)-4-piperidinyl]methyl}-1-piperidinecarboxylate
Reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[CH2:3][CH2:2]1.[CH:21](I)([CH3:23])[CH3:22].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH3:22][CH:21]([N:1]1[CH2:2][CH2:3][CH:4]([CH2:7][CH:8]2[CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:12][CH2:13]2)[CH2:5][CH2:6]1)[CH3:23]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
1,1-Dimethylethyl 4-(4-piperidinylmethyl)-1-piperidinecarboxylate (may be prepared as described in Description 2) (3 g), isopropyl iodide (3.2 ml) and K2CO3 (2.94 g) were combined in acetonitrile (70 ml) and the reaction mixture heated at 50° C. overnight. The reaction was allowed to cool to room temperature, filtered and evaporated. The residue was dissolved in diethylether (50 ml) and washed successively with water (50 ml), saturated sodium thiosulphate solution (50 ml), saturated brine (50 ml) and dried (Na2SO4). The solvent was evaporated to give the title compound (D3) as a pale yellow oil (3.1 g).
Workup
- temperatureto cool to room temperature
- filtrationfiltered
- customevaporated
- dissolutionThe residue was dissolved in diethylether (50 ml)
- washwashed successively with water (50 ml), saturated sodium thiosulphate solution (50 ml), saturated brine (50 ml)
- dry with materialdried (Na2SO4)
- customThe solvent was evaporated
Sources & evidence
- ORD record
- ord-64d3a6b4d34046f9998aafb24779ff0f
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07638631B2
Reaction notes
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