Caprolactam → 1-[4-(Heptylamino)butyl]azepan-2-one

HRID 1639122Notes

Reaction equation

HRID 1639122 reaction equation
[H-].[Na+].[NH:3]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:4]1=[O:10].Br[CH2:12][CH2:13][CH2:14][CH2:15]Br.[CH2:17]([NH2:24])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>C1(C)C=CC=CC=1.C1C=CC=CC=1>[CH2:17]([NH:24][CH2:12][CH2:13][CH2:14][CH2:15][N:3]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:4]1=[O:10])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

7

Reactant 4

HCID 7768CaprolactamHCID 80561,4-DibromobutaneHCID 81271-HeptanamineHCID 24758Sodium hydride

Product 1

HCID 146259301-[4-(Heptylamino)butyl]azepan-2-oneYield 70.8%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 1140TolueneSolvent2×

Procedure

A mixture of 0.88 g of 60% sodium hydride and 200 ml of dry toluene was incorporated dropwise with a solution of 2.26 g of azacycloheptane-2-one in toluene, heated under reflux for one hour, thereafter incorporated with 17.3 g of 1,4-dibromobutane, further refluxed for 18 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 an oily substance. A mixture of 3.92 g of the thus obtained oily substance, 1.82 g of n-heptylamine and 50 ml of benzene was incorporated dropwise with 2.64 g of 1,8-diazabicyclo [5,4,0] undecene-7 (DBU) in benzene and agitated at room temperature for a whole day. The thus obtained reaction mixture (liquid state) was washed with water, dried, freed from the solvent by distillation off at reduced pressure and then finally distilled to obtain 3.16 g of colorless 1-[4-(n-heptylamino) butyl] 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 at reduced pressure
  9. distillationfinally distilled
  10. customto obtain an oily substance
  11. customThe thus obtained reaction mixture (liquid state)
  12. washwas washed with water
  13. customdried
  14. distillationfreed from the solvent by distillation off at reduced pressure
  15. distillationfinally distilled

Sources & evidence

ORD record
ord-ac02bf17223642fb8bde916fac411a1a
Source dataset
uspto-grants-1989_11
Patent number
US04882359

Reaction notes

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