Water → HCID 11379632, compound

HRID 2356378

Reaction equation

HRID 2356378 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.[C:13]1([SH:19])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:13]1([S:19][CH2:2][CH:3]2[C:8](=[O:9])[CH:7]3[CH2:10][CH2:11][N:4]2[CH2:5][CH2:6]3)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7969ThiophenolHCID 184012841-Azabicyclo(2.2.2)octan-3-one, 2-methylene-, hydrochloride (1:1)

Product 1

HCID 11379632HCID 11379632, compound

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 2-methylene-3-quinuclidinone hydrochloride (1 g, 0.0057 mol) in water (10 ml) triethylamine (1.73 g, 0.0171 mol), tetra-n-butyl ammonium bromide (180 mg, 0.00057 mol) and thiophenol (0.63 g, 0.0057 mol) were added and the reaction mixture was allowed to stir at 80° C. for 18 h. The completion of reaction was monitored by tlc. The reaction mixture was quenched with ice-cold water (20 ml), extracted with dichloromethane (4×50 ml), organic layers were washed with brine and dried over sodium sulphate, filtered and concentrated to get the crude product which was purified (550 mg) by column chromatography on silica gel using chloroform as eluent.

Workup

  1. customThe completion of reaction
  2. customThe reaction mixture was quenched with ice-cold water (20 ml)
  3. extractionextracted with dichloromethane (4×50 ml), organic layers
  4. washwere washed with brine
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9d07993715534551b8d96edf27dfb81b
Source dataset
uspto-grants-2010_07
Patent number
US07759361B2

Linked notes

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