Methyl iodide → 3-ethyl-1,3,9,10,11,12-hexahydro-1-methyl-2H-quino[4,3,2-ef][1,4]benzoxazepin-2-one

HRID 981939Notes

Reaction equation

HRID 981939 reaction equation
[CH2:1]([CH:3]1[C:9](=[O:10])[NH:8][C:7]2=[C:11]3[C:16](=[N:17][C:18]4=[CH:19][CH:20]=[CH:21][C:5](=[C:6]24)[O:4]1)[CH2:15][CH2:14][CH2:13][CH2:12]3)[CH3:2].[CH3:22]C(C)([O-])C.[K+].CI>O1CCCC1>[CH2:1]([CH:3]1[C:9](=[O:10])[N:8]([CH3:22])[C:7]2=[C:11]3[C:16](=[N:17][C:18]4=[CH:19][CH:20]=[CH:21][C:5](=[C:6]24)[O:4]1)[CH2:15][CH2:14][CH2:13][CH2:12]3)[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 537311453-Ethyl-1,3,9,10,11,12-hexahydro-2H-quino[4,3,2-ef][1,4]benzoxazepin-2-one

Product 1

HCID 538029823-ethyl-1,3,9,10,11,12-hexahydro-1-methyl-2H-quino[4,3,2-ef][1,4]benzoxazepin-2-oneYield 68.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 3-ethyl-1,3,9,10,11,12-hexahydro-2H-quino[4,3,2-ef][1,4]benzoxazepin-2-one (5.0 g) in dry tetrahydrofuran (150 ml) was added potassium t-butoxide (3.0 g), with stirring. After 20 mins, methyl iodide (1.66) was added, and the reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated, diluted with saturated potassium carbonate solution, and extracted with 2-butanone. The organic extracts were dried over anhydrous magnesium sulfate and concentrated. The residue was adhered to silica (methanol) and flash chromatographed (50% ethyl acetate/hexane). The appropriate fractions were concentrated and the residue was triturated with diethyl ether to give 3.59 g (68%) of 3-ethyl-1,3,9,10,11,12-hexahydro-1-methyl-2H-quino[4,3,2-ef][1,4]benzoxazepin-2-one.

Workup

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with saturated potassium carbonate solution
  4. extractionextracted with 2-butanone
  5. dry with materialThe organic extracts were dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customchromatographed (50% ethyl acetate/hexane)
  8. concentrationThe appropriate fractions were concentrated
  9. customthe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-c11380e153fe4a15862ae3c067dc87fd
Source dataset
uspto-grants-1991_02
Patent number
US04994452

Reaction notes

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