Hydrochloric Acid → HCID 54487876, compound

HRID 263264Notes

Reaction equation

HRID 263264 reaction equation
C1O[C:4]([CH2:6][CH2:7][CH2:8][N:9]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)(C)OC1.Cl.[CH2:26]([OH:28])[CH3:27]>>[CH2:17]([N:9]([CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH2:8][CH2:7][CH2:6][CH2:27][C:26]([CH2:4][CH2:6][CH2:7][CH2:8][N:9]([CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:28])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 21316515HCID 21316515, compound

Product 1

HCID 54487876HCID 54487876, compound

Procedure

A solution of N,N-dibenzyl-5-amino-pentan-2-one ethylene acetal (90 g) in ethanol (500 ml) containing dilute hydrochloric acid (200 ml) was refluxed for 1 hour. The solution was allowed to cool and the ethanol was evaporated in vacuo. The residue was dissolved in water and extracted with ether. The aqueous layer was made alkaline with dilute sodium hydroxide solution and was extracted twice with ether. The combined ethereal extracts were washed with water, dried over anhydrous sodium sulphate and evaporated in vacuo, to give a brown oil. The product was purified by chromatography to give N,N-dibenzyl-3-aminopropylmethyl ketone as a red-brown oil (60 g).

Workup

  1. temperaturewas refluxed for 1 hour
  2. temperatureto cool
  3. customthe ethanol was evaporated in vacuo
  4. dissolutionThe residue was dissolved in water
  5. extractionextracted with ether
  6. extractionwas extracted twice with ether
  7. washThe combined ethereal extracts were washed with water
  8. dry with materialdried over anhydrous sodium sulphate
  9. customevaporated in vacuo
  10. customto give a brown oil
  11. customThe product was purified by chromatography

Sources & evidence

ORD record
ord-43f4abd68a4e48a6b31bd69df402e7e1
Source dataset
uspto-grants-1979_05
Patent number
US04156730

Reaction notes

Loading…