Trifluoroacetic acid → HCID 9981209, compound

HRID 1586987Notes

Reaction equation

HRID 1586987 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%

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-915d42b933ff4ceea2e4d3c881559f0f
Source dataset
uspto-grants-1993_06
Patent number
US05216164

Reaction notes

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