Water → 1-Phenyl-cyclopropylamine

HRID 1986869Notes

Reaction equation

HRID 1986869 reaction equation
C(OC(=O)[NH:5][C:6]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:8][CH2:7]1)C.O.[OH-].[Na+]>C(O)CO>[C:9]1([C:6]2([NH2:5])[CH2:8][CH2:7]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 57722667HCID 57722667, compound

Product 1

HCID 1945491-Phenyl-cyclopropylamineYield 8.4%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
110 °C

Procedure

To a suspension of 0.84 g (4.1 mmol) of the above carbamate in a 1:2 mixture of H2O:ethylene glycol (4.5 mL) was added 1.0 g (25 mmol) of sodium hydroxide as a solid in one portion. The slurry was heated to 110° C. for 15 h during which time a solid precipitated out of solution. The mixture was cooled to room temperature and poured into a solution of 2N HCl (30 mL). The mixture was washed with Et2O and the aqueous layer made basic to pH 12 by addition of 6N NaOH. The aqueous phase was washed with CH2Cl2 and the combined organic phase was dried over anhydrous Na2SO4 and concentrated under reduced pressure to provide 0.046 g (8%) of 1-phenyl -cyclopropylamine as a clear oil. m/z cacld. C9H12N [M+H]+: 134.20. Found: 133.90.

Workup

  1. customprecipitated out of solution
  2. temperatureThe mixture was cooled to room temperature
  3. additionpoured into a solution of 2N HCl (30 mL)
  4. washThe mixture was washed with Et2O
  5. additionthe aqueous layer made basic to pH 12 by addition of 6N NaOH
  6. washThe aqueous phase was washed with CH2Cl2
  7. dry with materialthe combined organic phase was dried over anhydrous Na2SO4
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5ab00588ce4943e69a979e9856358f50
Source dataset
uspto-grants-2009_06
Patent number
US07550473B2

Reaction notes

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