1-Iodopropane → HCID 54239688, compound
Reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]2[C@@H:6]3[C@@H:11]([CH2:12][CH2:13][C:4]=2[CH:3]=1)[NH:10][C:9](=[O:14])[CH2:8][CH2:7]3.[CH2:17](I)[CH2:18][CH3:19]>C1COCC1.[OH-].[Na+]>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]2[C@@H:6]3[C@@H:11]([CH2:12][CH2:13][C:4]=2[CH:3]=1)[N:10]([CH2:17][CH2:18][CH3:19])[C:9](=[O:14])[CH2:8][CH2:7]3Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
A 2.35 g portion of (4aR)-(10bR)-8-chloro-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one was slurried in 40 mL of THF and 5 mL of 50% aqueous sodium hydroxide, and 3.4 g of propyl iodide was added. The mixture was heated to about 60°, and the mixture was stirred at that temperature for about 22 hours. Workup was carried out by separating the organic layer and evaporating it to dryness, and adding water and ethyl acetate. The organic layer was separated, washed twice with water, dried, filtered and evaporated under vacuum to obtain 710 mg of white crystalline product, found to be of about 90% purity. It was then purified by silica gel flash chromatography, eluting with ethyl acetate, to obtain 510 mg of purified product, m.p. 110-11°, of 98.98% purity, by HPLC, eluting with 1:1 acetonitrile:aqueous buffer (5% ammonium acetate) and monitoring at 220 nanometers.
Workup
- temperatureThe mixture was heated to about 60°
- customby separating the organic layer
- customevaporating it to dryness
- additionadding water and ethyl acetate
- customThe organic layer was separated
- washwashed twice with water
- customdried
- filtrationfiltered
- customevaporated under vacuum
Sources & evidence
- ORD record
- ord-024e7e053cb14fb391f6089cc3e70cee
- Source dataset
- uspto-grants-2000_11
- Patent number
- US06150375
Reaction notes
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