Hydrochloric Acid → 4-Dimethylamino-4-(3-methoxypropyl)-cyclohexanone

HRID 1948613Notes

Reaction equation

HRID 1948613 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1([N:16]([CH3:18])[CH3:17])[CH2:15][CH2:14][C:9]2(OCC[O:10]2)[CH2:8][CH2:7]1.Cl>O>[CH3:18][N:16]([CH3:17])[C:6]1([CH2:5][CH2:4][CH2:3][O:2][CH3:1])[CH2:7][CH2:8][C:9](=[O:10])[CH2:14][CH2:15]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68842849[8-(3-Methoxypropyl)-1,4-dioxa-spiro[4.5]dec-8-yl]-dimethylamine

Product 1

HCID 686977404-Dimethylamino-4-(3-methoxypropyl)-cyclohexanone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

[8-(3-methoxypropyl)-1,4-dioxa-spiro[4.5]dec-8-yl]-dimethylamine (8.11 g, 31.5 mmole) was dissolved in water (12 ml), conc. HCl (19.5 ml) was added while cooling with ice, and the reaction mixture was stirred for 3 days at room temperature. The reaction mixture was washed with ether (2×75 ml). The solution was then made alkaline with 5N NaOH and extracted with dichloromethane (3×75 ml). The combined organic phases were washed with water (75 ml), dried over Na2SO4, filtered, and the solvent was removed in vacuo.

Workup

  1. temperaturewhile cooling with ice
  2. washThe reaction mixture was washed with ether (2×75 ml)
  3. extractionextracted with dichloromethane (3×75 ml)
  4. washThe combined organic phases were washed with water (75 ml)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-c971fd508e5d4cfe814aecda0586b03f
Source dataset
uspto-grants-2013_03
Patent number
US08399503B2

Reaction notes

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