Water → 2-(2-Phenylethyl)morpholine

HRID 596300Notes

Reaction equation

HRID 596300 reaction equation
[C:1]1([CH2:7][CH2:8][CH:9]2[O:14][CH2:13][C:12](=O)[NH:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1.CCOCC>[C:1]1([CH2:7][CH2:8][CH:9]2[O:14][CH2:13][CH2:12][NH:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 20354762HCID 20354762, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 199643972-(2-Phenylethyl)morpholine

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(β-phenylethyl)morpholine-5-one (430 mg.) in dry tetrahydrofuran (4 ml.) is added to a stirred suspension of lithium aluminium hydride (200 mg.) in dry ether (20 ml.) at such a rate that the mixture refluxes gently. After complete addition, the mixture is stirred and refluxed for 2 hours, then it is cooled and there are successively added water (0.2 ml.), sodium hydroxide solution (2N, 0.2 ml.) and water (0.6 ml.) and stirring is continued for 15 minutes. The mixture is filtered and the filtrate is evaporated under reduced pressure to give 2-(β-phenylethyl)morpholine as an oil which may be converted to its hydrogen oxalate salt, m.p. 151°-152° C. or its hydrogen maleate salt, m.p. 120°-122° C. on recrystallisation from methanol/ethyl acetate.

Workup

  1. additionAfter complete addition
  2. temperaturerefluxed for 2 hours
  3. temperatureit is cooled
  4. stirringstirring
  5. filtrationThe mixture is filtered
  6. customthe filtrate is evaporated under reduced pressure

Sources & evidence

ORD record
ord-d73aabbfaa3843a5b83ec68985a8a337
Source dataset
uspto-grants-1977_03
Patent number
US04010266

Reaction notes

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