Morpholine → 4-(4-methoxybenzyl)morpholine

HRID 650044Notes

Reaction equation

HRID 650044 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Cl)=[CH:5][CH:4]=1.[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chloride

Product 1

HCID 7824394-(4-methoxybenzyl)morpholine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Methyoxybenzylchloride (25 g, 0.16 mol), morpholine (14 g, 0.16 mol), and potassium carbonate (22 g, 0.16 mol) were taken up in acetonitrile and Kl (8.7 g, 0.04 mol) added. The reaction mixture was heated at reflux for 18 h, filtered, and the filtrate concentrated and azeotropped with benzene to give 17.5 g (88%) as an oil; IR(film, υ=cm−1) 2956, 2806, 1514, 1246, 1118, 866; 1H NMR (300 MHz, DMSO-d6) δ 2.29 (4H, br. s), 3.35 (2H, s), 3.53 (4H, t, J=4.4 Hz), 3.71 (3H, s), 6.86 (2H, d, J=8.5 Hz), 7.19 (2H, d, J=8.5 Hz); MS(DCl)m/z: 208 (MH+).

Workup

  1. additionKl (8.7 g, 0.04 mol) added
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for 18 h
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated and azeotropped with benzene
  6. customto give 17.5 g (88%) as an oil

Sources & evidence

ORD record
ord-8f8279bb8ca54afb9fd291e63fbc6b4f
Source dataset
uspto-grants-2001_08
Patent number
US06271249B1

Reaction notes

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