Butyl bromide → 1-butylazepane
Reaction equation
[NH:1]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:8](Br)[CH2:9][CH2:10][CH3:11]>>[CH2:8]([N:1]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[CH2:9][CH2:10][CH3:11]Participants
3
Reactant 2
Product 1
Procedure
The first N-substitution of azepane was carried out using butyl bromide as an N-alkylating agent to form 1-butylazepane. An equimolar amount of butyl bromide was added dropwise to a solution of azepane 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 0.90 (t, 3H), 1.28 (sextet, 2H), 1.42 (m, 2H), 1.60 (broad m, 8H), 2.42 (m, 2H), 2.60 (m, 4H).
Sources & evidence
- ORD record
- ord-72e1cb7a40bb4a1dabcd6e7276b31d56
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08088917B2
Reaction notes
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