Trifluoroacetic acid → HCID 55097307, compound

HRID 1443919Notes

Reaction equation

HRID 1443919 reaction equation
[CH3:1][C:2]([CH3:18])([CH3:17])[CH2:3][C:4]([NH:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[CH:12][CH:11]=[CH:10]2)=[O:5].FC(F)(F)C(O)=O>[Pt].C(O)C>[CH3:1][C:2]([CH3:18])([CH3:17])[CH2:3][C:4]([NH:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH2:12][CH2:11][CH2:10]2)=[O:5]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59168391HCID 59168391, compound

Product 1

HCID 55097307HCID 55097307, compoundYield 86.1%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3,3-dimethyl-N-quinolin-6-ylbutanamide (2.4 g), 5% platinum on carbon (0.15 g), trifluoroacetic acid (2.0 mL) and ethanol (50 mL) was hydrogenated at 45 PSI on a Parr shaker for 48 h. The reaction mixture was filtered through Celite® and the filtrate was concentrated. The crude solid was dissolved in ethyl acetate and washed carefully with saturated aqueous sodium bicarbonate. The organic layer was dried (MgSO4) and concentrated. The resulting oil was dissolved in ether and 4 N HCl was added. The solid was collected by filtration to yield 3,3-dimethyl-N-1,2,3,4-tetrahydroquinolin-6-ylbutanamide (2.1 g) as its HCl salt. MS (ES) m/z 247.2.

Workup

  1. filtrationThe reaction mixture was filtered through Celite®
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe crude solid was dissolved in ethyl acetate
  4. washwashed carefully with saturated aqueous sodium bicarbonate
  5. dry with materialThe organic layer was dried (MgSO4)
  6. concentrationconcentrated
  7. dissolutionThe resulting oil was dissolved in ether
  8. addition4 N HCl was added
  9. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-06850061aeae4f61b835daed3f92e1c4
Source dataset
uspto-grants-2010_02
Patent number
US07662831B2

Reaction notes

Loading…