Acetic Acid → HCID 22767572, compound

HRID 1111671Notes

Reaction equation

HRID 1111671 reaction equation
[CH3:1][C:2]1([CH3:13])[C:6]2([CH2:9][C:10](=O)[CH3:11])[CH2:7][CH2:8][CH:3]1[CH2:4][CH2:5]2.C(O)(=O)C.[CH3:18][NH2:19]>[Pt]=O.C(O)C>[CH3:18][NH:19][CH:10]([CH3:11])[CH2:9][C:6]12[C:2]([CH3:13])([CH3:1])[CH:3]([CH2:8][CH2:7]1)[CH2:4][CH2:5]2

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 6329MethylamineHCID 13039163HCID 13039163, compound

Product 1

HCID 22767572HCID 22767572, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

A mixture of 7,7-dimethyl-1-(2-oxo-n-propyl) norbornane (4.69 g), glacial acetic acid (10 ml), methylamine (10g) and ethanol (100 ml) was heated under reflux for 1 hour, cooled to room temperature and hydrogenated for 4 hours at 4 atmospheres using platinum oxide (0.25 g) as catalyst. The catalyst was removed by filtration and the filtrate evaporated to low volume before extracting with ether. The aqueous phase was basified with 2N-sodium hydroxide solution and the liberated base extracted into ether. The combined extracts were washed with water, dried (MgSO4) and evaporated in vacuo to yield the title product (4.15 g) which was characterised as the hydrochloride salt.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hour
  3. customThe catalyst was removed by filtration
  4. customthe filtrate evaporated to low volume
  5. extractionbefore extracting with ether
  6. extractionthe liberated base extracted into ether
  7. washThe combined extracts were washed with water
  8. dry with materialdried (MgSO4)
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-631f33a8fa774e4a88314c2a84cbac61
Source dataset
uspto-grants-1978_10
Patent number
US04118499

Reaction notes

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