Potassium Carbonate → HCID 131720618, compound

HRID 1599374Notes

Reaction equation

HRID 1599374 reaction equation
[CH2:1]=[CH:2][CH:3]1[CH:8]2[CH2:9][CH:10]([C@H:11]([OH:23])[C:12]3[CH:21]=[CH:20][N:19]=[C:18]4[C:13]=3[CH:14]=[C:15]([OH:22])[CH:16]=[CH:17]4)[N:5]([CH2:6][CH2:7]2)[CH2:4]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:31][C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][CH:39]=1)[C:35]#[N:36]>CC(C)=O.CN(C)C=O.C1OCCOCCOCCOCCOCCOC1>[C:35]([C:34]1[CH:33]=[C:32]([CH:39]=[CH:38][CH:37]=1)[CH2:31][O:22][C:15]1[CH:14]=[C:13]2[C:18]([N:19]=[CH:20][CH:21]=[C:12]2[C@H:11]([OH:23])[C@@H:10]2[N:5]3[CH2:6][CH2:7][C@H:8]([C@@H:3]([CH:2]=[CH2:1])[CH2:4]3)[CH2:9]2)=[CH:17][CH:16]=1)#[N:36]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 51196O-DesmethylquinidineHCID 97249Benzonitrile, 3-(bromomethyl)-

Product 1

HCID 131720618HCID 131720618, compoundYield 79.1%

Reagents, catalysts & solvents 3

HCID 2855718-Crown-6CatalystHCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.6 g (1.91 mmol) of 6-hydroxycinchonine in 25 ml of anhydrous acetone (dried and distilled over potassium carbonate) and 8 ml of anhydrous dimethylformamide is added 0.516 g (2.87 mmol) of anhydrous potassium carbonate followed by 0.329 g (1.91 mmol) of 3-(bromomethyl)benzonitrile (Lancaster) and 4 mg of 18-crown-6. The reaction mixture is heated to reflux for 18 h, cooled and filtered. The filtrate is concentrated under reduced pressure and redissolved in 200 ml of chloroform. The organic layer is washed with 2×50 ml of 5% aqueous sodium hydroxide, washed with brine, dried with anhydrous magnesium sulphate to yield 0.647 g (1.51 mmol, 79%) of (9S)-6'-(3-cyanobenzyloxy) cinchonane-9-ol as pale off-white solids.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 18 h
  3. temperaturecooled
  4. filtrationfiltered
  5. concentrationThe filtrate is concentrated under reduced pressure
  6. dissolutionredissolved in 200 ml of chloroform
  7. washThe organic layer is washed with 2×50 ml of 5% aqueous sodium hydroxide
  8. washwashed with brine
  9. dry with materialdried with anhydrous magnesium sulphate

Sources & evidence

ORD record
ord-9c0bbefd83624d3091dc229d43e548d3
Source dataset
uspto-grants-1998_04
Patent number
US05741715

Reaction notes

Loading…