Potassium Carbonate → 1-{4-[(4-Fluorophenyl)methyl]morpholin-3-yl}methanamine

HRID 1598385Notes

Reaction equation

HRID 1598385 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:24]=[CH:23][C:11]([CH2:12][N:13]2[CH2:18][CH2:17][O:16][CH2:15][C:14]2=[CH:19][N+:20]([O-])=O)=[CH:10][CH:9]=1.[OH-].[Na+].C(=O)([O-])[O-].[K+].[K+]>O.C1COCC1>[NH2:20][CH2:19][CH:14]1[CH2:15][O:16][CH2:17][CH2:18][N:13]1[CH2:12][C:11]1[CH:23]=[CH:24][C:8]([F:7])=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydride3×HCID 54068038HCID 54068038, compound

Product 1

HCID 189333781-{4-[(4-Fluorophenyl)methyl]morpholin-3-yl}methanamineYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To THF (200 ml) was added a small amount of lithium aluminum hydride, the solvent was dried, lithium aluminum hydride (2.0 g, 53 mmol) was suspended and the mixture was stirred at room temperature. Crystals of 4-(p-fluorobenzyl)-3-nitromethylidenemorpholine (6.58 g, 26.1 mmol) was added gradually and the mixture was stirred at room temperature. A further amount of lithium aluminum hydride (1.3 g, 34 mmol) was added and the mixture was stirred for one hour. Water (3.3 ml), 40% aqueous NaOH (3.3 ml) and water (10 ml) were added in turn and then potassium carbonate (40 g) was added followed by stirring. The reaction mixture was filtered and distilled off. The residue was dissolved in chloroform, dried over potassium carbonate and then the chloroform was distilled off to give 5.44 g of 3-aminomethy-4-(p-fluorobenzyl)morpholine as an oily substance. Yield=93%.

Workup

  1. customthe solvent was dried
  2. stirringthe mixture was stirred at room temperature
  3. stirringthe mixture was stirred for one hour
  4. stirringby stirring
  5. filtrationThe reaction mixture was filtered
  6. distillationdistilled off
  7. dissolutionThe residue was dissolved in chloroform
  8. dry with materialdried over potassium carbonate
  9. distillationthe chloroform was distilled off

Sources & evidence

ORD record
ord-edfcefce95b94145b868512cf996e758
Source dataset
uspto-grants-1998_04
Patent number
US05736550

Reaction notes

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