1-Amino-2-propanol → HCID 69204386, compound

HRID 2116741Notes

Reaction equation

HRID 2116741 reaction equation
[NH2:1][CH2:2][CH:3]([OH:5])[CH3:4].[O:6]1[CH:8]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH2:7]1>C(#N)C>[CH2:8]([C:7]12[O:6][CH:8]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH2:7][N:1]1[CH2:2][CH:3]([CH3:4])[O:5]2)[CH2:9][CH2:10][CH3:11]

Participants

4

Reactant 2

HCID 41-Amino-2-propanolHCID 181262-Hexyloxirane

Product 1

HCID 69204386HCID 69204386, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
180 °C

Procedure

Under atmospheric nitrogen, 30.79 g of 1-amino-2-propanol was added drop-wise to a solution of 52.59 g of 1,2-epoxyoctane (in a ratio of 1:1 mol) in acetonitrile (100 g). The mixture was stirred and eventually solidified followed by the removal of acetonitrile in vacuum. Under atmospheric nitrogen, 30.00 g of valeric acid and the product of the first step, 83.33 g of 2-(2-hydroxypropylamino)octan-1-ol (in a ratio of 1:1.5 mol) were added to a flask with a Dean Stark trap and a condenser. The reaction mixture was heated to 180° C. and stirred. Water was collected in the trap. The reaction flask was connected to a distillation apparatus. At 180° C. and under a vacuum of 1.33 Pa, approximately 30 g were distilled over to a flask containing molecular sieves to absorb the final equivalent of water. The product was distilled from the reaction mixture and further purified by extraction with petroleum ether followed by distillation. The product, 7a-butyl-2-hexyl-6-methyl-tetrahydro-2H-oxazolo[2,3-b]oxazole, was isolated with 20% yield.

Workup

  1. customeventually solidified followed by the removal of acetonitrile in vacuum
  2. additionUnder atmospheric nitrogen, 30.00 g of valeric acid and the product of the first step, 83.33 g of 2-(2-hydroxypropylamino)octan-1-ol (in a ratio of 1:1.5 mol) were added to a flask with a Dean Stark trap and a condenser
  3. stirringstirred
  4. customWater was collected in the trap
  5. distillationAt 180° C. and under a vacuum of 1.33 Pa, approximately 30 g were distilled over to a flask
  6. additioncontaining molecular sieves
  7. customto absorb the final equivalent of water
  8. distillationThe product was distilled from the reaction mixture
  9. customfurther purified by extraction with petroleum ether
  10. distillationfollowed by distillation

Sources & evidence

ORD record
ord-437b1d9cf6c849a8bdda17969bb84c1a
Source dataset
uspto-grants-2008_10
Patent number
US07439354B2

Reaction notes

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