Methyl iodide → Hydrochloric Acid

HRID 364141Notes

Reaction equation

HRID 364141 reaction equation
[ClH:1].Br[C:3]1[CH:8]=[CH:7][C:6]2[C@H:9]3[CH2:14][CH2:13][CH2:12][N:11]([CH3:15])[C@@H:10]3[CH2:16][O:17][C:5]=2[C:4]=1[O:18][CH3:19].[C:20]([Li])(C)(C)C.CI>O1CCCC1.CCCCCC.C(OCC)(=O)C>[ClH:1].[ClH:1].[CH3:19][O:18][C:4]1[C:5]2[O:17][CH2:16][C@@H:10]3[C@@H:9]([C:6]=2[CH:7]=[CH:8][C:3]=1[CH3:20])[CH2:14][CH2:13][CH2:12][N:11]3[CH3:15]

Participants

8

Reactant 3

HCID 6328Methyl iodideHCID 86740946HCID 86740946, compoundHCID 178418306HCID 178418306, compound

Product 2

HCID 313Hydrochloric AcidHCID 86740944HCID 86740944, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2.3 g of trans-8-bromo-7-methoxy-4-methyl-1,2,3,4a,5,10b-hexahydro-4H-[1]-benzopyrano[3,4-b]pyridine (Example 21) in 45 ml of tetrahydrofuran at -70° is added 5.6 ml of 2.6M t-butyllithium in hexane. After 5 minutes at -70°, 1.36 g of methyl iodide is added. After warming to 0°, the reaction mixture is diluted with ethyl acetate and washed with water. After drying over magnesium sulfate the solvent is removed in vacuo. Acidification of the residue with ethanolic hydrochloric acid yields trans-7-methoxy-4,8-dimethyl-1,2,3,4a,5,10b-hexahydro-4H-[1]-benzopyrano[3,4-b]pyridine hydrochloride, m.p. 277°-278°.

Workup

  1. temperatureAfter warming to 0°
  2. washwashed with water
  3. dry with materialAfter drying over magnesium sulfate the solvent
  4. customis removed in vacuo

Sources & evidence

ORD record
ord-08211ce8bac94323bcd22c6acd216819
Source dataset
uspto-grants-1986_08
Patent number
US04604397

Reaction notes

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