HCID 10362064, compound → HCID 19026196, compound

HRID 1195161Notes

Reaction equation

HRID 1195161 reaction equation
[CH3:1][Li].[C:3]1([CH2:9][O:10][NH:11][C:12]2([CH3:30])[CH2:21][CH2:20][CH2:19][C:18]3[N:17]=[C:16]([O:22][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH:15]=[CH:14][C:13]2=3)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>O1CCCC1>[C:3]1([CH2:9][O:10][N:11]([CH3:1])[C:12]2([CH3:30])[CH2:21][CH2:20][CH2:19][C:18]3[N:17]=[C:16]([O:22][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH:15]=[CH:14][C:13]2=3)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 10362064HCID 10362064, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 19026196HCID 19026196, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyllithium (1.4M in diethyl ether, 37.7 ml) was added dropwise over 20 min to a solution of N,2-bis(phenylmethoxy)-5,6,7,8-tetrahydro-5-methyl-5-quinolinamine (18.1 g) and tetrahydrofuran (20 ml) at -78° C. The mixture was allowed to warm to room temperature over 2 hrs and was stirred at room temperature for an additional 1 hr. The solution was quenched with saturated ammonium chloride solution and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous potassium carbonate, filtered, and the filtrate was concentrated. The residue was purified by high performance liquid chromatography (silica gel, elution with ethyl acetate-hexanes) to provide 12.3 g (65%) of product.

Workup

  1. customThe solution was quenched with saturated ammonium chloride solution
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous potassium carbonate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by high performance liquid chromatography (silica gel, elution with ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-ca98b3389153432dbdb3677424b1f6e5
Source dataset
uspto-grants-1992_05
Patent number
US05110815

Reaction notes

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