Furan, 2-(bromomethyl)tetrahydro- → HCID 13023237, compound
Reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]23[CH2:16][CH2:15][CH2:14][CH:13]2[CH2:12][NH:11][CH2:10][CH2:9]3)[CH:5]=[CH:6][CH:7]=1.C(=O)(O)[O-].[Na+].[O:22]1[CH2:26][CH2:25][CH2:24][CH:23]1[CH2:27]Br>CN(C)C=O>[OH:1][C:2]1[CH:3]=[C:4]([C:8]23[CH2:16][CH2:15][CH2:14][CH:13]2[CH2:12][N:11]([CH2:27][CH:23]2[CH2:24][CH2:25][CH2:26][O:22]2)[CH2:10][CH2:9]3)[CH:5]=[CH:6][CH:7]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
A solution of 1.5 g. of 4a-(3-hydroxyphenyl)-2,3,4,4a,5,6,7,7a-octahydro-1H-2-pyrindine in 15 ml. of N,N-dimethylformamide containing 1.0 g. of sodium bicarbonate and 0.95 g. of 2-tetrahydrofurylmethyl bromide was heated at reflux for four hours. After cooling the reaction mixture to about 25° C., the mixture was extracted several times with diethyl ether. The ethereal extracts were combined, washed with water, and dried. Removal of the solvent by evaporation under reduced pressure provided 4a-(3-hydroxyphenyl)-2-(2-tetrahydrofurylmethyl)-2,3,4,4a,5,6,7,7a-octahydro-1H-2-pyrindine as an oil. The oil so formed was dissolved in diethyl ether and added to a solution of hydrogen bromide gas in diethyl ether. The product crystallized out of solution and was collected by filtration to provide 1.0 g. of 4a-(3-hydroxyphenyl)-2-(2-tetrahydrofurylmethyl)-2,3,4,4a,5,6,7,7a-octahydro-1H-2-pyrindinium bromide. M.P. 190°-192° C.
Workup
- temperatureat reflux for four hours
- extractionthe mixture was extracted several times with diethyl ether
- washwashed with water
- customdried
- customRemoval of the solvent
- customby evaporation under reduced pressure
Sources & evidence
- ORD record
- ord-3db46367fcb34d9cb605c75e928e5754
- Source dataset
- uspto-grants-1982_06
- Patent number
- US04337341
Reaction notes
Loading…