Dichloromethane → 2-Methylene-3-quinuclidone

HRID 1017647Notes

Reaction equation

HRID 1017647 reaction equation
Cl.O.O.[CH2:4]=[C:5]1[C:10](=[O:11])[CH:9]2[CH2:12][CH2:13][N:6]1[CH2:7][CH2:8]2.C([O-])([O-])=O.[K+].[K+].C(Cl)Cl>O>[CH2:4]=[C:5]1[C:10](=[O:11])[CH:9]2[CH2:12][CH2:13][N:6]1[CH2:7][CH2:8]2

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 219542752-Methylene-3-quinuclidinone dihydrate hydrochloride

Product 1

HCID 3229732-Methylene-3-quinuclidoneYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-methylene-3-quinuclidinone dihydrate hydrochloride (25.7 g, 0.1225 mol, 1 eq) and K2CO3 (67.0 g, 0.4848 mol, 4 eq) is dissolved in 125 mL water and 200 mL CH2Cl2 and stirred vigorously. After 16 h, the layers are separated and the aqueous layer is extracted with CH2Cl2. The combined organic layers are dried over MgSO4, filtered and concentrated to give 14.75 g (88%) of 2-methylenequinuclidin-3-one as a yellow oil. MS (ES) for C8H11 NO m/z 138.1 (M+H)+.

Workup

  1. customthe layers are separated
  2. extractionthe aqueous layer is extracted with CH2Cl2
  3. dry with materialThe combined organic layers are dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-284d1909a2bd487a879ac434e410d423
Source dataset
uspto-grants-2002_11
Patent number
US06479510B2

Reaction notes

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