Acetonitrile → HCID 35813066, compound

HRID 736290Notes

Reaction equation

HRID 736290 reaction equation
C(=O)([O-])[O-].[K+].[K+].C(#N)C.[OH:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([NH2:17])=[O:16])=[CH:13][CH:12]=1.Cl.Cl[CH2:22][CH2:23][N:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1>CN(C)C=O>[N:24]1([CH2:23][CH2:22][O:10][C:11]2[CH:19]=[CH:18][C:14]([C:15]([NH2:17])=[O:16])=[CH:13][CH:12]=2)[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 650524-HydroxybenzamideHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)

Product 1

HCID 35813066HCID 35813066, compoundYield 23.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (15.1 g, 109 mmol, 3 eq.), acetonitrile (73 mL) and then 4-hydroxybenzamide (5 g, 36.5 mmol, 1 eq.) are placed in a 250 mL round-bottomed flask. The suspension is stirred for 30 minutes, followed by addition of 4-(2-chloroethyl)morpholine hydrochloride (8.82 g, 47 mmol, 1.3 eq.). 10 mL of dimethylformamide are added to this suspension, and the mixture is then stirred at a temperature in the region of 40° C. for 16 hours. The solvent is then evaporated off and the residue is diluted with water and extracted with dichloromethane. The aqueous phase is acidified with 5 N hydrochloric acid and reextracted with dichloromethane. The organic phases are combined, dried over magnesium sulfate and then concentrated to dryness under vacuum. 4-(2-Morpholin-4-ylethoxy)benzamide 2.17 g (23%) is thus obtained in the form of a white solid, which is used directly in the following step.

Workup

  1. stirringthe mixture is then stirred at a temperature in the region of 40° C. for 16 hours
  2. customThe solvent is then evaporated off
  3. additionthe residue is diluted with water
  4. extractionextracted with dichloromethane
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated to dryness under vacuum

Sources & evidence

ORD record
ord-e03b06c6a37d4c2f9cb201b1c7a232a1
Source dataset
uspto-grants-2009_09
Patent number
US07595320B2

Reaction notes

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