Methyl iodide → HCID 19697551, compound

HRID 863256Notes

Reaction equation

HRID 863256 reaction equation
[H-].[K+].[CH2:3]([N:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH:12]([CH2:20][OH:21])[CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:22]I>O1CCCC1>[CH2:3]([N:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH:12]([CH2:20][O:21][CH3:22])[CH2:11]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 82127Potassium hydrideHCID 19697838HCID 19697838, compound

Product 1

HCID 19697551HCID 19697551, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.3 g of a potassium hydride suspension (20% in oil) are added to a solution of 2.6 g of 1-benzyl-3(R,S)-hydroxymethyl-1,2,3,4-tetrahydroquinoline in 30 ml of tetrahydrofuran at 0° C., while stirring, and 1.9 ml of methyliodide are then added. After 1 h, the reaction mixture is concentrated and the residue is purified over 160 g of silica gel with a 20:1 mixture of hexane and ethyl acetate. 1-Benzyl-3(R,S)-methoxymethyl-1,2,3,4-tetrahydroquinoline is obtained as a yellow solid: Rf (20:1 mixture of hexane and ethyl acetate)=0.32. A solution of 2.9 g of the product thus obtained in 30 ml of tetrahydrofuran is hydrogenated in the presence of 0.6 g of palladium-on-charcoal under the customary conditions. Purification of the crude product over 80 g of silica gel with methylene chloride as the eluting agent gives 3(R,S)-methoxymethyl-1,2,3,4-tetrahydroquinoline: Rf (methylene chloride)=0.32; Rf (A)=0.56.

Workup

  1. concentrationthe reaction mixture is concentrated
  2. customthe residue is purified over 160 g of silica gel with a 20:1 mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-9ecc37cdecc34790b15c329811ce6de7
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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