Acetic Acid → HCID 68683092, compound

HRID 1716442Notes

Reaction equation

HRID 1716442 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.C(O)(=O)C.[C:9]([C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1)(=O)[CH2:10][CH3:11].C([BH3-])#N.[Na+]>CO>[CH:1]1([NH:4][CH:9]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[CH2:10][CH3:11])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 69828CyclopropylamineHCID 743431-(4-Pyridinyl)-1-propanoneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 68683092HCID 68683092, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a mixture of 8 g of molecular sieves and 8.4 g (148 mmol) of cyclopropylamine in 100 ml of methanol at 0° C., were successively added 11 ml of acetic acid and 10 g (74 mmol) of 4-propionyl-pyridine. The reaction mixture was stirred for 3 hrs at reflux and cooled to room temperature. A solution of 6.9 g (185 mmol) of sodium cyanoborohydride in 20 ml of methanol was added dropwise. The reaction mixture was stirred for 3 hrs at reflux, and cooled to room temperature. The reaction mixture was concentrated in vacuum to half its volume and diluted with 80 ml of dichloromethane. Heptane was added so that a solid precipitated. The solid was filtrated. The filtrate was concentrated in vacuum to give 8.7 g (66%) of N-cyclopropyl-1-pyridin-4-yl-propylamine.

Workup

  1. temperatureat reflux
  2. stirringThe reaction mixture was stirred for 3 hrs
  3. temperatureat reflux
  4. temperaturecooled to room temperature
  5. concentrationThe reaction mixture was concentrated in vacuum to half its volume
  6. additiondiluted with 80 ml of dichloromethane
  7. additionHeptane was added so that a solid
  8. customprecipitated
  9. filtrationThe solid was filtrated
  10. concentrationThe filtrate was concentrated in vacuum

Sources & evidence

ORD record
ord-2387582a01ca413a90dcaa0dac8e0047
Source dataset
uspto-grants-2010_09
Patent number
US07803821B2

Reaction notes

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