Sodium Hydroxide → (4-Benzylmorpholin-2-yl)methanamine

HRID 1598366Notes

Reaction equation

HRID 1598366 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([CH2:14][N:15]2C(=O)C3=CC=CC=C3C2=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN.[OH-].[Na+]>C(O)C>[NH2:15][CH2:14][CH:10]1[O:11][CH2:12][CH2:13][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:9]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 117245602-((4-benzylmorpholin-2-yl)methyl)-2,3-dihydro-1H-isoindole-1,3-dione

Product 1

HCID 2776360(4-Benzylmorpholin-2-yl)methanamineYield 109.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of crude 4-benzyl-2-phthalimidomethylmorpholine (64 g) in ethanol (500 ml) was added hydrazine monohydrate (18 ml, 0.57 mol) and the mixture was heated under reflux for 2 hours. After cooling, 10% aqueous sodium hydroxide (200 ml) was added to dissolve insolubles and the ethanol was distilled off under reduced pressure. The aqueous layer was extracted with chloroform (200 ml×3), the combined organic layer was dried over potassium carbonate and the solvent was distilled off to give crude 2-aminomethyl-4-benzylmorpholine (42.97 g). This compound was used for the subsequent reaction without purification.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. temperatureAfter cooling
  4. dissolutionto dissolve insolubles
  5. distillationthe ethanol was distilled off under reduced pressure
  6. extractionThe aqueous layer was extracted with chloroform (200 ml×3)
  7. dry with materialthe combined organic layer was dried over potassium carbonate
  8. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-0604300661a148f2810ebdd76f4b6df4
Source dataset
uspto-grants-1998_04
Patent number
US05736550

Reaction notes

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