1-Iodopropane → HCID 54239688, compound

HRID 1079120Notes

Reaction equation

HRID 1079120 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]3

Participants

5

Reactant 2

HCID 336431-IodopropaneHCID 100599928-Chloro-1,4,4a,5,6,10b-hexahydro-2H-benzo[f]quinolin-3-one

Product 1

HCID 54239688HCID 54239688, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

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. Analysis calculated for C16H20NClO: C, 69,18; H, 7.26; N, 5.04 Found: C, 68.92; H, 7.09; N, 5.15

Workup

  1. temperatureThe mixture was heated to about 60°
  2. customby separating the organic layer
  3. customevaporating it to dryness
  4. additionadding water and ethyl acetate
  5. customThe organic layer was separated
  6. washwashed twice with water
  7. customdried
  8. filtrationfiltered
  9. customevaporated under vacuum

Sources & evidence

ORD record
ord-2682fe2a5f22442295430ff5cca6e8c2
Source dataset
uspto-grants-1996_08
Patent number
US05550134

Reaction notes

Loading…