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

HRID 1809664Notes

Reaction equation

HRID 1809664 reaction equation
[O:1]=[C:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:3][C:4]#[N:5].[OH-].[Na+]>C1COCC1>[NH2:5][CH2:4][CH2:3][CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:1]

Participants

4

Conditions

Temperature
25 °C

Procedure

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 3-amino-1-phenyl-propan-1-ol. (Yield 30 g, crude).

Workup

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

Sources & evidence

ORD record
ord-26cf154121b9405b9f15a8e0be77b9da
Source dataset
uspto-grants-2013_01
Patent number
US08362023B2

Reaction notes

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