Sulfuric Acid → cis-(+/-)-1-n-Propyl-7-oxodecahydroquinoline

HRID 255511Notes

Reaction equation

HRID 255511 reaction equation
C[O:2][C:3]1[CH2:8][CH:7]=[C:6]([CH2:9][CH2:10][CH2:11][NH:12][CH2:13][CH2:14][CH3:15])[CH2:5][CH:4]=1.S(=O)(=O)(O)O.[OH-].[Na+]>>[CH2:13]([N:12]1[C@@H:7]2[C@@H:6]([CH2:5][CH2:4][C:3](=[O:2])[CH2:8]2)[CH2:9][CH2:10][CH2:11]1)[CH2:14][CH3:15]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 136504211-Methoxy-4-(3-n-propylamino)propyl-1,4-cyclohexadiene

Product 1

HCID 67935530cis-(+/-)-1-n-Propyl-7-oxodecahydroquinolineYield 22.7%

Procedure

One hundred twenty-one grams of 1-methoxy-4-(3-n-propylamino)propyl-1,4-cyclohexadiene were dissolved in 1 l. of 15% aqueous sulfuric acid. The acidic solution was refluxed for about 6 hours and was then poured over ice. The dilute acidic solution was made basic with 50% aqueous sodium hydroxide. The now-basic aqueous solution was extracted with methylene dichloride. The methylene dichloride extract was dried and the solvent removed therefrom to yield 25.6 g of cis-(±)-1-n-propyl-7-oxodecahydroquinoline.

Workup

  1. temperatureThe acidic solution was refluxed for about 6 hours
  2. additionwas then poured over ice
  3. extractionThe now-basic aqueous solution was extracted with methylene dichloride
  4. extractionThe methylene dichloride extract
  5. customwas dried
  6. customthe solvent removed

Sources & evidence

ORD record
ord-e8ff7381d0d94aa3aac29d6ede4795b5
Source dataset
uspto-grants-1987_10
Patent number
US04698347

Reaction notes

Loading…