Potassium Carbonate → 1280565-71-0

HRID 1838590Notes

Reaction equation

HRID 1838590 reaction equation
Cl[CH2:2][CH2:3][CH2:4][OH:5].C(=O)([O-])[O-].[K+].[K+].[CH3:12][CH:13]1[O:18][CH:17]([CH3:19])[CH2:16][NH:15][CH2:14]1>C(#N)C>[CH3:19][C@H:17]1[CH2:16][N:15]([CH2:2][CH2:3][CH2:4][OH:5])[CH2:14][C@@H:13]([CH3:12])[O:18]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123133-Chloro-1-propanolHCID 1108622,6-Dimethylmorpholine

Product 1

HCID 532160581280565-71-0Yield 28.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-Chloro-1-propanol (1.04 g, 11 mmol) followed by potassium carbonate (2.07 g, 15 mmol) was added to a solution of 2,6-dimethylmorpholine (1.15 g, 10 mmol), (supplied by Aldrich Chemical Company Limited as a mixture of isomers), in acetonitrile (15 ml). The mixture was heated at reflux overnight and allowed to cool, the insolubles were removed by filtration and the volatiles were removed from the filtrate by evaporation. The residue was purified by column chromatography on silica eluting with methylene chloride/acetonitrile/methanol (60/35/5 followed by 60/30/10) to give cis-3-(2,6-dimethylmorpholino)-1-propanol (500 mg).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. temperatureto cool
  4. customthe insolubles were removed by filtration
  5. customthe volatiles were removed from the filtrate by evaporation
  6. customThe residue was purified by column chromatography on silica eluting with methylene chloride/acetonitrile/methanol (60/35/5 followed by 60/30/10)

Sources & evidence

ORD record
ord-342394f4b5434cb483397e9e13a41d29
Source dataset
uspto-grants-2004_01
Patent number
US06673803B2

Reaction notes

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