Methyl iodide → HCID 54394200, compound

HRID 1195786Notes

Reaction equation

HRID 1195786 reaction equation
[C:1](O)(=O)/[CH:2]=[CH:3]/[C:4]([OH:6])=O.C1(C2[CH2:21][NH:20][C:19]3=[C:22]4[C:27](=[N:28][C:29]5=[CH:30][CH:31]=[CH:32][C:17](=[C:18]35)[O:16]2)[CH2:26][CH2:25][CH2:24][CH2:23]4)C=CC=CC=1.C[C:34]([CH3:37])([O-])[CH3:35].[K+].[CH3:39]I.[Cl-].[NH4+]>O1CCCC1>[CH3:21][N:20]1[C:19]2=[C:22]3[C:27](=[N:28][C:29]4=[CH:30][CH:31]=[CH:32][C:17](=[C:18]24)[O:16][CH:3]([C:2]2[CH:1]=[CH:37][CH:34]=[CH:35][CH:39]=2)[C:4]1=[O:6])[CH2:26][CH2:25][CH2:24][CH2:23]3

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxideHCID 67757352HCID 67757352, compound

Product 1

HCID 54394200HCID 54394200, compoundYield 100.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,3,9,10,11,12-Hexahydro-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-c817b2a745f740548d49b20a08d024b6
Source dataset
uspto-grants-1992_05
Patent number
US05112829

Reaction notes

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