Sodium Hydroxide → 3-Amino-1-phenylpropan-1-ol

HRID 1186503Notes

Reaction equation

HRID 1186503 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[O:7]=[C:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:9][C:10]#[N:11].[OH-].[Na+]>C1COCC1>[NH2:11][CH2:10][CH2:9][CH:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[OH:7]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 64799BenzoylacetonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 1215483-Amino-1-phenylpropan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
25 °C

Procedure

To a stirred suspension of LAH (20 g, 517 mmol) in dry THF (500 mL) was added a solution of 3-oxo-3-phenylpropanenitrile (30 g, 207 mmol) in dry THF (300 mL) drop-wise at 0° C. under nitrogen atmosphere. The mixture was warmed to 25° C. and then heated at 70° C. for 2 hours. After cooling to 0° C., a saturated solution of sodium hydroxide was added drop-wise and extracted with dichloromethane (200 mL). The organic solution was dried over anhydrous sodium sulfate and concentrated to dryness. The residue was purified by column chromatography (methanol:dichloromethane, 1:10) to afford crude 3-amino-1-phenyl-propan-1-ol. (Yield 30 g). LC-MS: [M+H]+ 152.

Workup

  1. temperatureheated at 70° C. for 2 hours
  2. temperatureAfter cooling to 0° C.
  3. extractionextracted with dichloromethane (200 mL)
  4. dry with materialThe organic solution was dried over anhydrous sodium sulfate
  5. concentrationconcentrated to dryness
  6. customThe residue was purified by column chromatography (methanol:dichloromethane, 1:10)

Sources & evidence

ORD record
ord-5855c57f0b0844d29e14104545076235
Source dataset
uspto-grants-2014_03
Patent number
US08673905B2

Reaction notes

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