4-Morpholineacetonitrile → 2-Morpholinoethylamine

HRID 56156Notes

Reaction equation

HRID 56156 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[O:7]1[CH2:12][CH2:11][N:10]([CH2:13][C:14]#[N:15])[CH2:9][CH2:8]1>C1COCC1.O>[O:7]1[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][NH2:15])[CH2:9][CH2:8]1

Participants

5

Reactant 2

HCID 220554-MorpholineacetonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 4082852-MorpholinoethylamineYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To anhydrous THF (35 mL) was added LiAlH4 (3.19 g, 84 mmol) in one portion in an ice bath. The mixture was stirred at 0° C. for 20 min, and a solution of 2-morpholinoacetonitrile (3.50 g, 28 mmol) in anhydrous THF (10 mL) was added dropwise. Upon the end of addition the mixture was refluxed for 3 h, then cooled to rt, diluted with water (20 mL), filtered and concentrated in vacuo to give the title compound as yellow oil (2.62 g, 72%).

Workup

  1. additionUpon the end of addition the mixture
  2. temperaturewas refluxed for 3 h
  3. temperaturecooled to rt
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-47efaf3b4a92420ebfa47bd4a3bcd64d
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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