Water → HCID 19881040, compound

HRID 847392Notes

Reaction equation

HRID 847392 reaction equation
[S:1]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6](=[O:12])[NH:5][C:4]=2[CH:3]=[CH:2]1.CC(C)([O-])C.[K+].Br[CH2:20][CH2:21][CH2:22][CH2:23][Cl:24].O>CN(C)C=O>[Cl:24][CH2:23][CH2:22][CH2:21][CH2:20][N:5]1[C:6](=[O:12])[CH2:7][CH2:8][CH2:9][CH2:10][C:11]2[S:1][CH:2]=[CH:3][C:4]1=2

Participants

6

Reactant 4

HCID 962WaterHCID 813641-Bromo-4-chlorobutaneHCID 6682266,7,8,9-Tetrahydrothieno[3,2-b]azocin-5(4H)-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 19881040HCID 19881040, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2.0 g of 6,7,8,9-tetrahydrothieno[3,2-b]azocin-5(4H)-one in 20 ml of dimethylformamide was added 1.3 g of potassium t-butoxide under ice-cooling and stirred at the same temperature. To the mixture was added 2.0 g of 1-bromo-4-chlorobutane and stirred at room temperature for 5 hours. The mixture was poured into water and extracted ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was chromatographed on a silica gel using a chloroform as an eluent to give 2.8 g of 4-(4-chlorobutyl)-6,7,8,9-tetrahydrothieno[3,2-b]azocin-5(4H)-one as a pale yellow oil.

Workup

  1. temperaturecooling
  2. stirringstirred at room temperature for 5 hours
  3. extractionextracted ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed on a silica gel using a chloroform as an eluent

Sources & evidence

ORD record
ord-f20a1d30bef24e559d9f9a44b0ecc102
Source dataset
uspto-grants-1992_08
Patent number
US05141930

Reaction notes

Loading…