Water → HCID 58899552, compound

HRID 2356374Notes

Reaction equation

HRID 2356374 reaction equation
[CH2:1]=[C:2]1[C:7](=[O:8])[CH:6]2[CH2:9][CH2:10][N:3]1[CH2:4][CH2:5]2.O.C([N:14]([CH2:17][CH3:18])[CH2:15][CH3:16])C>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[N:14]1([CH2:1][CH:2]2[C:7](=[O:8])[CH:6]3[CH2:9][CH2:10][N:3]2[CH2:4][CH2:5]3)[C:15]2[C:16](=[CH:1][CH:2]=[CH:7][CH:6]=2)[CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 3229732-Methylene-3-quinuclidone

Product 1

HCID 58899552HCID 58899552, compound

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 2-methylene-3-quinuclidinone (0.5 g, 0.0028 mol) in water (6 ml) indoline (0.66 g, 0.0057 mol), triethylamine (0.84 g, 0.0084 mol) and tetra-n-butyl ammonium bromide (90 mg, 0.00028 mol) were added and the reaction mixture were allowed to stir at 80° C. for 18-20 h. The reaction mixture was quenched with ice-cold water (20 ml), extracted with dichloromethane (3×50 ml), the organic layers were washed with brine and dried over sodium sulphate, filtered and concentrated to get the crude product which was purified as greenish yellow solids (125 mg, 17%) by column chromatography on neutral silica gel using chloroform as eluent.

Workup

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

Sources & evidence

ORD record
ord-f192cefeaa964ae48c0958a4eafe332f
Source dataset
uspto-grants-2010_07
Patent number
US07759361B2

Reaction notes

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