HCID 18623221, compound → 3-(3,4-Difluorophenyl)morpholine

HRID 278926Notes

Reaction equation

HRID 278926 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[F:7][C:8]1[CH:9]=[C:10]([CH:15]2[NH:20][C:19](=O)[CH2:18][O:17][CH2:16]2)[CH:11]=[CH:12][C:13]=1[F:14]>CCOCC.C1COCC1>[F:7][C:8]1[CH:9]=[C:10]([CH:15]2[NH:20][CH2:19][CH2:18][O:17][CH2:16]2)[CH:11]=[CH:12][C:13]=1[F:14]

Participants

5

Reactant 2

HCID 18623221HCID 18623221, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 186232193-(3,4-Difluorophenyl)morpholine

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of LiAlH4 (6.0 mmol, 0.23 g) in 25.0 mL of Et2O was added a solution of 5-(3,4-difluoro-phenyl)-morpholin-3-one (2.0 mmol, 0.42 g) in 20.0 mL Et2O and 5.0 mL THF at room temperature. The resulting suspension was heated to reflux for 2 hours and was then quenched with water and aq. NaOH solution. The solid was filtered off and the filtrate was dried over Na2SO4. The filtrate was then decanted and the solvent was removed in vacuo to obtain 5-(3,4-difluoro-phenyl)-morpholine as a viscous oil. It was converted to its hydrochloride salt for its analysis. Yellow powder. M.P.=171-173° C.; Mass spec. 200 (M+1, 100%). Analysis calculated for C10H12NOF2Cl.0.5 acetone: C, 51.96; H, 5.61; N, 5.41. Found: C, 51.98; H, 5.70; N, 5.34.

Workup

  1. temperatureThe resulting suspension was heated
  2. temperatureto reflux for 2 hours
  3. customwas then quenched with water and aq. NaOH solution
  4. filtrationThe solid was filtered off
  5. dry with materialthe filtrate was dried over Na2SO4
  6. customThe filtrate was then decanted
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-c6cdbf0a64174b12acb5666fe5d1551e
Source dataset
uspto-grants-2002_03
Patent number
US06362182B1

Reaction notes

Loading…