4-Methylmorpholine → N-[4-(4-Hydroxy-phenoxy)-benzyl]-propionamide

HRID 49152Notes

Reaction equation

HRID 49152 reaction equation
[NH2:1][CH2:2][C:3]1[CH:16]=[CH:15][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.CN1CCOCC1.[C:24](Cl)(=[O:27])[CH2:25][CH3:26]>C(#N)C>[OH:14][C:11]1[CH:12]=[CH:13][C:8]([O:7][C:6]2[CH:15]=[CH:16][C:3]([CH2:2][NH:1][C:24](=[O:27])[CH2:25][CH3:26])=[CH:4][CH:5]=2)=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 62324Propionyl chlorideHCID 20636236HCID 20636236, compound

Product 1

HCID 20636237N-[4-(4-Hydroxy-phenoxy)-benzyl]-propionamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-(4-Aminomethyl-phenoxy)-phenol (0.10 g, 0.47 mmol), MMP-resin (polystyrene bound N-methylmorpholine-type base, 0.30 g, 1.04 mmol) and 1.9 mL of acetonitrile was treated with propionyl chloride (0.086 mL, 1.0 mmol) and shaken for 24 hours at room temperature. After filtration of the resin, the filtrate was diluted with 2 mL of methanol and was treated with 2 mL of 1M lithium hydroxide (LiOH) in water. The mixture was shaken for 24 hours at room temperature, treated with Amberlite IRP-64® resin until neutral, filtered and concentrated in vacuo, affording N-[4-(4-Hydroxy-phenoxy)-benzyl]-propionamide. MS (m/z): 272.2 [M+H]+.

Workup

  1. filtrationAfter filtration of the resin
  2. additionthe filtrate was diluted with 2 mL of methanol
  3. additionwas treated with 2 mL of 1M lithium hydroxide (LiOH) in water
  4. stirringThe mixture was shaken for 24 hours at room temperature
  5. additiontreated with Amberlite IRP-64® resin until neutral,
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-75350c41cd7e499796319afe0614f444
Source dataset
uspto-grants-2004_03
Patent number
US06706723B2

Reaction notes

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