Potassium Carbonate → HCID 37979251, compound

HRID 576866Notes

Reaction equation

HRID 576866 reaction equation
[C:1]1([C@H:7]([NH2:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:11][CH:12]([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:14]([O:13][CH:12]([O:16][CH2:17][CH3:18])[CH2:11][NH:9][C@@H:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:8])[CH3:15]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 6431891-Phenethylamine, (+)-

Product 1

HCID 37979251HCID 37979251, compoundYield 71.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (R)-(+)-1-phenylethylamine 66.6 g (550 mmol) in acetonitrile 300 ml, 2-bromo-1,1-diethoxyethane 41.3 ml (270 mmol) and potassium carbonate 70.7 g (405 mmol) were added and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated in vacuo and the residue was diluted with ethyl acetate 300 ml and washed with water 500 ml and brine 500 ml. The organic phase was dried with magnesium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was purified on silica gel column chromatography (n-hexane:ethyl acetate=5:1 and 1:1) to obtain the title compound 46.0 g (70%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionthe residue was diluted with ethyl acetate 300 ml
  3. washwashed with water 500 ml and brine 500 ml
  4. dry with materialThe organic phase was dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe residue was purified on silica gel column chromatography (n-hexane:ethyl acetate=5:1 and 1:1)

Sources & evidence

ORD record
ord-6db027be56234413b9e60d51e9e7ef0a
Source dataset
uspto-grants-2015_05
Patent number
US09040531B2

Reaction notes

Loading…