Benzyl Bromide → (1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)methanol
Reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:9][CH2:10][C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1.[BH4-].[Na+]>CN(C)C=O.C(O)C>[CH2:1]([N:14]1[CH2:13][CH:12]=[C:11]([CH2:10][OH:9])[CH2:16][CH2:15]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
Procedure
10.7 ml (0.0901 mol) of benzyl bromide were added to a solution of 8.9 g (0.0815 mol) of 4-hydroxymethylpyridine in 30 ml of dimethylformamide and the mixture was stirred at 100° for 2 hours. Subsequently, the reaction mixture was cooled to room temperature, diluted with 111 ml of ethanol and treated portion-wise with 3.9 g (0.103 mol) of NaBH4. The mixture was boiled under reflux for 3 hours and stirred at room temperature for a further 18 hours. Then, the solvent was distilled off, the residue was partitioned between dichloromethane/water, extracted and dried. After removal of the solvent the residue was chromatographed on silica gel with ethyl acetate/hexane 1:1 as the eluent. 9.26 g (56%) of (1-benzyl-1,2,3,6-tetrahydro-pyridin-4-yl)-methanol were obtained as yellow crystals; m.p. 57°-60°.
Workup
- temperatureunder reflux for 3 hours
- stirringstirred at room temperature for a further 18 hours
- distillationThen, the solvent was distilled off
- customthe residue was partitioned between dichloromethane/water
- extractionextracted
- customdried
- customAfter removal of the solvent the residue
- customwas chromatographed on silica gel with ethyl acetate/hexane 1:1 as the eluent
Sources & evidence
- ORD record
- ord-af6a9b5d15b344d5bec14c4e2caab594
- Source dataset
- uspto-grants-1997_11
- Patent number
- US05688798
Reaction notes
Loading…