Butyl bromide → 1-Butyl-3-methylpiperidine
Reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][NH:4][CH2:3]1.[CH2:8](Br)[CH2:9][CH2:10][CH3:11]>>[CH2:8]([N:4]1[CH2:5][CH2:6][CH2:7][CH:2]([CH3:1])[CH2:3]1)[CH2:9][CH2:10][CH3:11]Participants
3
Procedure
The first N-substitution of 3-methylpiperidine was carried out using butyl bromide as an N-alkylating agent to form 1-butyl-3-methylpiperidine. An equimolar amount of butyl bromide was added dropwise to a solution of 3-methylpiperidine in methanol keeping the temperature at 20° C. by an ice-water bath. The mixture was hydrolyzed with potassium carbonate, extracted with ether, and dried over Na2SO4. The solution was fractionally distilled at reduced pressure and the fraction with bp 195° C. was collected. 1H-NMR (300 MHz, CDCl3) δ 0.82 (d, 3H), 0.90 (t, 3H), 1.30 (m, 2H), 1.48 (m, 2H), 1.65 (m, 5H), 2.24 (m, 2H), 2.82 (m, 4H).
Sources & evidence
- ORD record
- ord-e8f5a8c8313042e6a7209890ef95e6a6
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08088917B2
Reaction notes
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