1-Octanol → 1-[3-(Octyloxy)propyl]azepan-2-one

HRID 1639121Notes

Reaction equation

HRID 1639121 reaction equation
[H-].[Na+].Br[CH2:4][CH2:5][CH2:6]Br.[NH:8]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C:9]1=[O:15].[CH2:16]([OH:24])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>C1(C)C=CC=CC=1>[CH2:16]([O:24][CH2:4][CH2:5][CH2:6][N:8]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C:9]1=[O:15])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

6

Reactant 4

HCID 9571-OctanolHCID 7768CaprolactamHCID 80011,3-DibromopropaneHCID 24758Sodium hydride2×

Product 1

HCID 140104921-[3-(Octyloxy)propyl]azepan-2-oneYield 69.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A mixture of 0.93 g of 60% sodium hydride and 100 ml of dry toluene was incorporated dropwise with 3.00 g of n-octyl alcohol, heated under reflux for one hour, thereafter incorporated with 14.1 g of 1,3-dibromopropane, further refluxed for 12 hours and then filtered to remove insoluble materials to obtain a filtrate. The thus obtained filtrate was washed with water, dried, freed from the solvent by distillation off and then finally distilled to obtain a colorless transparent substance. 4.59 g of the thus obtained substance was added to a mixture of 2.07 g of azacycloheptane-2-one, 0.80 g of 60% sodium hydride and 150 ml of dry toluene, after which the whole was refluxed for 12 hours and then filtered to remove insoluble materials to obtain a filtrate. The thus obtained filtrate was washed with water, dried, freed from the solvent by distillation off at reduced pressure and then finally distilled to obtain 3.60 g of colorless 1-[3-(n-octyloxy) propyl] azacycloheptane-2-one having the following appearance, column temperature and analysis:

Workup

  1. temperatureheated
  2. temperatureunder reflux for one hour
  3. filtrationfiltered
  4. customto remove insoluble materials
  5. customto obtain a filtrate
  6. washThe thus obtained filtrate was washed with water
  7. customdried
  8. distillationfreed from the solvent by distillation off and
  9. distillationthen finally distilled
  10. customto obtain a colorless transparent substance
  11. temperatureafter which the whole was refluxed for 12 hours
  12. filtrationfiltered
  13. customto remove insoluble materials
  14. customto obtain a filtrate
  15. washThe thus obtained filtrate was washed with water
  16. customdried
  17. distillationfreed from the solvent by distillation off at reduced pressure
  18. distillationfinally distilled

Sources & evidence

ORD record
ord-a582f0c4a4ed4976b5e4418b6355f72e
Source dataset
uspto-grants-1989_11
Patent number
US04882359

Reaction notes

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