Ethyl Acetate → Cyclopropyl-pyridin-4-ylmethyl-amine

HRID 2092010Notes

Reaction equation

HRID 2092010 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.[N:5]1[CH:10]=[CH:9][C:8]([CH:11]=O)=[CH:7][CH:6]=1.[BH4-].[Na+].C(OCC)(=O)C>C(O)C>[N:5]1[CH:10]=[CH:9][C:8]([CH2:11][NH:4][CH:1]2[CH2:3][CH2:2]2)=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 133894-PyridinecarboxaldehydeHCID 69828CyclopropylamineHCID 4311764Sodium borohydride

Product 1

HCID 1080492Cyclopropyl-pyridin-4-ylmethyl-amineYield 126.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

Cyclopropylamine (69 μL, 0.99 mmol) in ethanol (1 mL) was mixed with 4-pyridinecarbaldehyde (86 μL, 0.99 mmol) at room temperature and refluxed at 90° C. for 2 hours. After completion of the reaction, the ethanol was evaporated azeotropically. The resulting reaction product in methanol (1 mL) was mixed with sodium borohydride (204 mg, 5.40 mmol) under cooling with ice and stirred at room temperature for 24 hours. After completion of the reaction, the reaction solution was mixed with ethyl acetate, and the organic layer was washed with saturated aqueous ammonium chloride, dried over anhydrous sodium sulfate and evaporated under reduced pressure to give the desired product (185 mg, quant.).

Workup

  1. customAfter completion of the reaction
  2. customthe ethanol was evaporated azeotropically
  3. customThe resulting reaction product in methanol (1 mL)
  4. temperatureunder cooling with ice
  5. customAfter completion of the reaction
  6. washthe organic layer was washed with saturated aqueous ammonium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-484bc802463c475988a7faeedb681f7b
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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