Trifluoroacetic acid → HCID 9981209, compound

HRID 1033510Notes

Reaction equation

HRID 1033510 reaction equation
FC(F)(F)C(O)=O.O[C:9]1([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:18][CH2:17][CH2:16][C:15]2[N:14]=[C:13]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:12]=[CH:11][C:10]1=2.[C:34]1([CH2:40][O:41][NH2:42])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C1(C)C=CC=CC=1>[C:34]1([CH2:40][O:41][NH:42][C:9]2([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:18][CH2:17][CH2:16][C:15]3[N:14]=[C:13]([O:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH:12]=[CH:11][C:10]2=3)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 102313O-BenzylhydroxylamineHCID 10315565HCID 10315565, compound

Product 1

HCID 9981209HCID 9981209, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Trifluoroacetic acid (16.6 g) was added in one portion to a solution of 5,6,7,8-tetrahydro-5-hydroxy-2-(phenylmethoxy)-5-(phenylmethyl)quinoline (50 g), phenylmethoxyamine (44.8 g), and toluene (600 ml) at room temperature. The solution was stirred at room temperature for 19 hrs, and the reaction mixture was quenched with conc ammonium hydroxide solution. The layers were separated and the aqueous phase was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over potassium carbonate, filtered, and the filtrate was concentrated. Purification by high performance liquid chromatography (silica gel, elution with ethyl acetate-hexanes) gave 40.0 g (61%) of 5,6,7,8-tetrahydro-N,2-bis(phenylmethoxy)-5-(phenylmethyl)-5-quinolinamine

Workup

  1. customthe reaction mixture was quenched with conc ammonium hydroxide solution
  2. customThe layers were separated
  3. extractionthe aqueous phase was extracted with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over potassium carbonate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated
  8. customPurification
  9. washby high performance liquid chromatography (silica gel, elution with ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-d81a9d073cff433b8c90a2a4751048de
Source dataset
uspto-grants-1994_05
Patent number
US05310914

Reaction notes

Loading…