Water → (8aR-trans)-octahydro-1-propyl-6(2H)-quinolinone

HRID 279958

Reaction equation

HRID 279958 reaction equation
O.CC1(C)CO[C:6]2([CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]2)OC1.[CH2:16]([NH2:19])[CH2:17][CH3:18].O.[C:21]1(C)[CH:26]=CC(S(O)(=O)=O)=C[CH:22]=1>C1(C)C=CC=CC=1>[CH2:16]([N:19]1[C@H:6]2[C@@H:9]([CH2:10][C:11](=[O:14])[CH2:12][CH2:13]2)[CH2:26][CH2:21][CH2:22]1)[CH2:17][CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 7852PropylamineHCID 521998p-Toluenesulfonic acid monohydrateHCID 5879683,3-Dimethyl-1,5-dioxaspiro(5.5)undecan-9-one

Product 1

HCID 13457872(8aR-trans)-octahydro-1-propyl-6(2H)-quinolinone

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A 250 ml single neck round bottom flask fitted with a water separator containing 20 g of 3A sieves (Linde) was charged with 100 ml of toluene, 10.25 g (0.052 mol) of 3,3-dimethyl-1,5-dioxaspiro[5.5]undecan-9-one (Aldrich Chemical Company), 17.97 g (3.04 mmol) of n-propylamine (Baker) and 18 mg (0.09 mmol) of p-toluenesulfonic acid monohydrate (Aldrich). The reaction mixture was refluxed for 24 hours and cooled, and the toluene was evaporated under reduced pressure to produce the title compound.

Workup

  1. temperatureThe reaction mixture was refluxed for 24 hours
  2. temperaturecooled
  3. customthe toluene was evaporated under reduced pressure

Sources & evidence

ORD record
ord-5a4c264c5471459b8d3a8fecca54cb00
Source dataset
uspto-grants-1986_05
Patent number
US04587351

Linked notes

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