Potassium Carbonate → 4-Methoxy-3-(3-morpholinopropoxy)benzonitrile

HRID 870513Notes

Reaction equation

HRID 870513 reaction equation
[N:1]1([CH2:7][CH2:8][CH2:9][OH:10])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.CS(Cl)(=O)=O.C(=O)([O-])[O-].[K+].[K+].O[C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][C:30]=1[O:31][CH3:32])[C:26]#[N:27]>ClCCl>[CH3:32][O:31][C:30]1[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][C:23]=1[O:10][CH2:9][CH2:8][CH2:7][N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 1995763-Morpholino-1-propanolHCID 49128223-Hydroxy-4-methoxybenzonitrile

Product 1

HCID 103560884-Methoxy-3-(3-morpholinopropoxy)benzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

5 g 3-Morpholine-4-yl-propan-1-ol was dissolved in dichloromethane, cooled to 0° C., 3.25 mL methanesulfonylchloride was added and the mixture was stirred for 2 h at ambient temperature. Then 7 g potassium carbonate and 3-hydroxy-4-methoxybenzonitrile were added and the reaction was stirred at 45° C. for 3 h. The mixture was concentrated and 70 mL dimethylacetamide was added and stirred at 120° C. for 3 h. After this time, the mixture was diluted with dichloromethane and extracted with water, the organic phase was dried over magnesium sulfate and concentrated.

Workup

  1. stirringthe reaction was stirred at 45° C. for 3 h
  2. concentrationThe mixture was concentrated
  3. addition70 mL dimethylacetamide was added
  4. stirringstirred at 120° C. for 3 h
  5. additionAfter this time, the mixture was diluted with dichloromethane
  6. extractionextracted with water
  7. dry with materialthe organic phase was dried over magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-cb0deb6bf76c46f5bd47bda1f5f51253
Source dataset
uspto-grants-2015_03
Patent number
US08969568B2

Reaction notes

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