Water → HCID 13289799, compound
Reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[Br:15][CH2:16][CH2:17][CH2:18][CH2:19]Br.[OH2:21].CN(C)C=[O:25]>>[CH2:1]([N:8]1[C:12](=[O:21])[CH2:11][N:10]([CH2:19][CH2:18][CH2:17][CH2:16][Br:15])[C:9]1=[O:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
Procedure
Benzylimidazoline of the preceding Example (1.9 g, 10 mmoles) in 5 ml of dimethylformamide was added dropwise to a slurry of sodium hydride (528 mg of 50% dispersion in oil, 11 mmoles) and the mixture then stirred for 1 hour at room temperature. The resulting solution was added dropwise to 1,4-dibromobutane (2.37 g, 11 mmole) in 10 ml of dimethylformamide. After stirring 16 hours at room temperature, the reaction mixture was poured into ice and water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered and evaporated to an oil. The oil was chromatographed on silica gel with chloroform as eluant. Clean product fractions were combined and evaporated to yield the title product as an oil [1.4 g, pnmr(CDCl3)delta 1.6-2.0 (m, 4H), 3.2-3.6 (m, 4H), 3.8 (s, 2H), 4.6 (s, 2H), 7.2-7.5 (m, 5H)].
Workup
- stirringAfter stirring 16 hours at room temperature
- extractionextracted with ethyl acetate
- washThe organic layer was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- customevaporated to an oil
- customThe oil was chromatographed on silica gel with chloroform as eluant
- customevaporated
Sources & evidence
- ORD record
- ord-0eb90729480a4caa8db69cb038b3076b
- Source dataset
- uspto-grants-1984_02
- Patent number
- US04432978
Reaction notes
Loading…