Water → (4-Chlorophenyl)(cyclopropyl)methanamine

HRID 423024Notes

Reaction equation

HRID 423024 reaction equation
O1CCCC1.B.CO[N:9]=[C:10]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)[CH:11]1[CH2:13][CH2:12]1.O.[OH-].[Na+]>C1COCC1>[Cl:20][C:17]1[CH:16]=[CH:15][C:14]([CH:10]([CH:11]2[CH2:12][CH2:13]2)[NH2:9])=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 2723981Borane;tetrahydrofuranHCID 73696106(4-chlorophenyl)(cyclopropyl)methanone O-methyl oxime2×

Product 1

HCID 5155531(4-Chlorophenyl)(cyclopropyl)methanamineYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Borane tetrahydrofuran complex (1N in THF, 65.6 mL) was added to (4-chlorophenyl)(cyclopropyl)methanone O-methyl oxime (Intermediate 2) (2.75 g) in THF (100 mL) at 25° C. under nitrogen. The resulting solution was stirred at reflux for 3 hours, then cooled to 0° C. Water was carefully added, followed by aqueous NaOH (20%, 100 mL). The resulting mixture was stirred at reflux overnight, then allowed to cool to room temperature. The product was extracted into hexane, then dried over sodium sulfate, filtered and evaporated to afford (4-chlorophenyl)(cyclopropyl)methanamine as a clear oil (2.205 g, 93%).

Workup

  1. temperatureat reflux for 3 hours
  2. stirringThe resulting mixture was stirred
  3. temperatureat reflux overnight
  4. temperatureto cool to room temperature
  5. extractionThe product was extracted into hexane
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-56fa5e93847f44a6a4ec4bcb8ece001f
Source dataset
uspto-grants-2012_01
Patent number
US08101623B2

Reaction notes

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