Water → Methyl(2-(morpholin-4-yl)ethyl)amine

HRID 2282445Notes

Reaction equation

HRID 2282445 reaction equation
C(O[C:6](=O)[NH:7][CH2:8][CH2:9][N:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)(C)(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[CH3:6][NH:7][CH2:8][CH2:9][N:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydride2×HCID 58930414tert-butyl N-[2-(morpholin-4-yl)ethyl]carbamate

Product 1

HCID 14979282Methyl(2-(morpholin-4-yl)ethyl)amineYield 103.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Intermediate 45a (6.0 g, 24.6 mmol) in THF (123 mL) was added lithium aluminium hydride (2.33 g, 61.5 mmol) portionwise, then the mixture was stirred at reflux for 4 h. A further portion of lithium aluminium hydride (1.28 g, 33.6 mmol) was added to the cooled solution, then the mixture was stirred at reflux for a further 8 h. Water (3.75 mL) was added dropwise, followed by 4N aqueous NaOH (11.3 mL) and water (3.75 ml). The mixture was filtered, washed with diethyl ether, dried (MgSO4) and concentrated in vacuo to give the title compound as a yellow oil (3.67 g, 99%). 1H NMR (400 MHz, CDCl3): 2.40-2.52 (9H, m), 2.67 (2H, t, J 2.7), 3.70 (4H, t, J 4.5).

Workup

  1. temperatureat reflux for 4 h
  2. stirringthe mixture was stirred
  3. temperatureat reflux for a further 8 h
  4. filtrationThe mixture was filtered
  5. washwashed with diethyl ether
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-678bb59137954dd493092865ed05cf12
Source dataset
uspto-grants-2015_09
Patent number
US09139584B2

Reaction notes

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