Butyl bromide → 1-Butyl-2,2,6,6-tetramethylpiperidin-4-ol
Reaction equation
[CH3:1][C:2]1([CH3:11])[CH2:7][CH:6]([OH:8])[CH2:5][C:4]([CH3:10])([CH3:9])[NH:3]1.Br[CH2:13][CH2:14][CH2:15][CH3:16]>>[CH2:13]([N:3]1[C:4]([CH3:10])([CH3:9])[CH2:5][CH:6]([OH:8])[CH2:7][C:2]1([CH3:11])[CH3:1])[CH2:14][CH2:15][CH3:16]Participants
Conditions
- Temperature
- -78 °C
Procedure
Into a 400-milliliter Hastalloy pressure tube are placed 62.8 grams of 2,2,6,6-tetramethyl-4-hydroxypiperidine and 35.6 grams of 1-bromobutane. The tube and contents are cooled to -78°C., evacuated and filled with nitrogen. The tube is sealed, shaken and warmed to 100°C. for 1 hour, 120°C. for 1 hour and 150°C. for 30 hours. The tube is cooled and the solid charge is removed and placed in a Soxlet extraction apparatus. The material is extracted for 8 hours with diethyl ether. The resulting ether solution is treated with activated charcoal, filtered and concentrated under vacuum. The residue is distilled at 120°-125°C. at 1 torr to give 26 grams of 1-(1-butyl)-2,2,6,6-tetramethyl-4-hydroxypiperidine, a white solid melting at 29°-33°C.
Workup
- customInto a 400-milliliter Hastalloy pressure tube are placed
- customevacuated
- additionfilled with nitrogen
- customThe tube is sealed
- temperaturewarmed to 100°C. for 1 hour, 120°C. for 1 hour and 150°C. for 30 hours
- temperatureThe tube is cooled
- additionthe solid charge
- customis removed
- extractionplaced in a Soxlet extraction apparatus
- extractionThe material is extracted for 8 hours with diethyl ether
- additionThe resulting ether solution is treated with activated charcoal
- filtrationfiltered
- concentrationconcentrated under vacuum
- distillationThe residue is distilled at 120°-125°C. at 1 torr
Sources & evidence
- ORD record
- ord-1f3e76f553ab487eb0c172298188d320
- Source dataset
- uspto-grants-1977_01
- Patent number
- US04001189
Reaction notes
Loading…