HCID 2802853, compound → 1-(Adamantan-1-yl)propan-2-amine

HRID 866548Notes

Reaction equation

HRID 866548 reaction equation
[C:1]12([CH2:11][C:12](=[N:14]O)[CH3:13])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2>O=[Pt]=O.C(O)(=O)C>[C:1]12([CH2:11][CH:12]([NH2:14])[CH3:13])[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

Participants

4

Reactant 1

HCID 2802853HCID 2802853, compound

Product 1

HCID 383751-(Adamantan-1-yl)propan-2-amine

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

1-Adamantyl-2-propanone oxime (59 gm.) was dissolved in 775 ml. acetic acid, 10 gm. PtO2 added and the mixture hydrogenated at about 40 lbs. pressure. The solution was filtered and concentrated. The residue was dissolved in 2 liters of ether, added, over 5-10 minutes, to 84 gm. NaHCO3 in 10 liters of water and stirred for 1/2 hour. The ether was separated and concentrated and the residue treated with 50 ml. acetic acid, and concentrated. The acetic acid residue was dissolved in 200 ml. ether, added to 8.4 gm. NaHCO3 in 1 liter of water and this solution added to the main solution. NaOH (53 ml. of 50% solution) was added to the combined aqueous solutions, stirred 5 minutes and extracted with 2 × 1.5 liters of ether. The ether extract was dried and concentrated and the residue distilled to give 42.2 gm. product, b25 161°.

Workup

  1. filtrationThe solution was filtered
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in 2 liters of ether
  4. additionadded, over 5-10 minutes, to 84 gm
  5. customThe ether was separated
  6. concentrationconcentrated
  7. additionthe residue treated with 50 ml
  8. concentrationacetic acid, and concentrated
  9. dissolutionThe acetic acid residue was dissolved in 200 ml
  10. additionether, added to 8.4 gm
  11. additionNaHCO3 in 1 liter of water and this solution added to the main solution
  12. additionNaOH (53 ml. of 50% solution) was added to the combined aqueous solutions
  13. stirringstirred 5 minutes
  14. extractionextracted with 2 × 1.5 liters of ether
  15. extractionThe ether extract
  16. customwas dried
  17. concentrationconcentrated
  18. distillationthe residue distilled
  19. customto give 42.2 gm
  20. customproduct, b25 161°

Sources & evidence

ORD record
ord-1ebf27aa412947d0b7829267dea9bc95
Source dataset
uspto-grants-1978_07
Patent number
US04100170

Reaction notes

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