Hexylamine → HCID 22141206, compound

HRID 1826429Notes

Reaction equation

HRID 1826429 reaction equation
Cl[CH2:2][CH:3]1[CH:5]([C:6]([O:8]CC)=O)[C:4]1([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]#[N:19])[CH:13]=1)[CH3:11].C(=O)([O-])O.[Na+].[CH2:25]([NH2:31])[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]>CN(C)C=O>[CH2:25]([N:31]1[CH2:2][CH:3]2[CH:5]([C:4]2([C:12]2[CH:13]=[C:14]([CH:15]=[CH:16][CH:17]=2)[C:18]#[N:19])[CH3:11])[C:6]1=[O:8])[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Participants

5

Reactant 3

HCID 8102HexylamineHCID 516892Sodium BicarbonateHCID 22141229HCID 22141229, compound

Product 1

HCID 22141206HCID 22141206, compoundYield 35.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 3-(chloromethyl)-2-(3-cyanophenyl)-2-methylcyclopropanecarboxylate (Preparation 35, 5.82 g, 21.1 mmol) in N,N-dimethylformamide (20 ml) at room temperature was added sodium hydrogen carbonate (1.77 g, 21.1 mmol) followed by hexylamine (16.7 ml, 0.13 mol). The mixture was then heated under reflux for 16 h, cooled to room temperature and poured onto ice. After warming to room temperature, the mixture was partitioned against diethyl ether (50 ml). The two layers were separated and the aqueous layer was extracted with diethyl ether (2×30 ml). The ethereal extracts were washed with water (50 ml), dried (MgSO4), filtered and concentrated in vacuo. The crude oil was purified by silica column chromatography eluting with a gradient of hexane:ethyl acetate (5:1 to 0:100) to afford the title compound (2.2 g, 35%) as a colourless oil.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureunder reflux for 16 h
  3. additionpoured onto ice
  4. temperatureAfter warming to room temperature
  5. customthe mixture was partitioned against diethyl ether (50 ml)
  6. customThe two layers were separated
  7. extractionthe aqueous layer was extracted with diethyl ether (2×30 ml)
  8. washThe ethereal extracts were washed with water (50 ml)
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customThe crude oil was purified by silica column chromatography
  13. washeluting with a gradient of hexane:ethyl acetate (5:1 to 0:100)

Sources & evidence

ORD record
ord-b968bf9a455a4c488326e193b0202579
Source dataset
uspto-grants-2006_05
Patent number
US07049444B2

Reaction notes

Loading…