1-Azabicyclo(2.2.2)octan-3-one, 2-methylene-, hydrochloride (1:1) → HCID 178515135, compound

HRID 2356377

Reaction equation

HRID 2356377 reaction equation
Cl.[CH2:2]=[C:3]1[C:8](=[O:9])[CH:7]2[CH2:10][CH2:11][N:4]1[CH2:5][CH2:6]2.O.[SH:13][C:14]1[N:22]=[CH:21][N:20]=[C:19]2[C:15]=1[NH:16][CH:17]=[N:18]2>O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[N:22]1[C:14]([S:13][CH2:2][CH:3]2[C:8](=[O:9])[CH:7]3[CH2:10][CH2:11][N:4]2[CH2:5][CH2:6]3)=[C:15]2[C:19]([NH:18][CH:17]=[N:16]2)=[N:20][CH:21]=1

Participants

5

Reactant 2

HCID 184012841-Azabicyclo(2.2.2)octan-3-one, 2-methylene-, hydrochloride (1:1)HCID 178527204HCID 178527204, compound

Product 1

HCID 178515135HCID 178515135, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

To a stirred solution of 2-methylene-3-quinuclidinone hydrochloride (0.5 g, 3.6 mmol) in water (6 ml) triethylamine (1.5 ml), tetra-n-butyl ammonium bromide (120 mg) and 6-mercapto-purine monohydrate (0.62 g) were added and the reaction mixture was allowed to stir at 85° C. for 14 h. The completion of reaction was monitored by tlc. The reaction mixture was quenched with ice-cold water (10 ml), extracted with dichloromethane (2×25 ml), the organic layers were washed with water, brine and dried over sodium sulphate, filtered and concentrated to get the crude product which was purified (140 mg, 14%) by flash column chromatography on neutral silica gel using 9:1 chloroform:methanol as eluent.

Workup

  1. customThe completion of reaction
  2. customThe reaction mixture was quenched with ice-cold water (10 ml)
  3. extractionextracted with dichloromethane (2×25 ml)
  4. washthe organic layers were washed with water, brine
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b2f85378e1124c06bba301649717b441
Source dataset
uspto-grants-2010_07
Patent number
US07759361B2

Linked notes

Loading…