Methyl iodide → HCID 54394200, compound

HRID 981943Notes

Reaction equation

HRID 981943 reaction equation
C(O)(=O)/C=C/C(O)=[O:5].[CH3:9][N:10]1[C:16]2=[C:17]3[C:22](=[N:23][C:24]4=[CH:25][CH:26]=[CH:27][C:14](=[C:15]24)[O:13][CH:12]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:11]1)[CH2:21][CH2:20][CH2:19][CH2:18]3.CC(C)([O-])C.[K+].CI.[Cl-].[NH4+]>O1CCCC1>[CH3:9][N:10]1[C:16]2=[C:17]3[C:22](=[N:23][C:24]4=[CH:25][CH:26]=[CH:27][C:14](=[C:15]24)[O:13][CH:12]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:11]1=[O:5])[CH2:21][CH2:20][CH2:19][CH2:18]3

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxideHCID 67946409HCID 67946409, compound

Product 1

HCID 54394200HCID 54394200, compoundYield 104%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,3,9,10,11,12-hexahydro-1-methyl-3-phenyl-2H-quino[4,3,2-ef][1,4]benzoxazepine fumarate (4.20 g) was suspended in dry tetrahydrofuran (75 ml), chilled with ice/water, and potassium tert-butoxide (1.50 g) was added. The mixture was stirred for 1 hr, methyl iodide (1.90 g) was added, and the mixture was stirred overnight. The reaction mixture was poured into ammonium chloride solution, and the organic layer was separated. The aqueous phase was extracted with ethyl acetate. The combined organic phase was dried over anhydrous magnesium sulfate, filtered, and the filtrate was evaporated. Recrystallization of the residue from methanol gave 3.37 g (77%) of product, mp 188°-189° C.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred overnight
  3. customthe organic layer was separated
  4. extractionThe aqueous phase was extracted with ethyl acetate
  5. dry with materialThe combined organic phase was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customthe filtrate was evaporated
  8. customRecrystallization of the residue from methanol

Sources & evidence

ORD record
ord-320359fd56cd4963b7b71289326fc6f8
Source dataset
uspto-grants-1991_02
Patent number
US04994452

Reaction notes

Loading…