Dimethylformamide → HCID 67899858, compound

HRID 1110349Notes

Reaction equation

HRID 1110349 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][C:5]2=[N:6][C:7]=1[CH:8]([C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1)O.[H-].[Na+].[H][H].CI.CN(C)[CH:30]=[O:31]>O>[CH3:1][C:2]1[CH:3]=[C:4]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][C:5]2=[N:6][C:7]=1[CH2:8][C:10]1([O:31][CH3:30])[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH2:11]1

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 9882188HCID 9882188, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67899858HCID 67899858, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-(6,7,8,9-Tetrahydro-3-methyl-5H-cyclohepta[b]pyrid-2-yl)-1-(4-methylphenyl)methanol (2.0 g 0.007 m) was added to sodium hydride (0.35 g, 50% dispersion in oil, 0.007M, washed with 40-60 petrol) suspended in dimethylformamide (20 ml). After evolution of hydrogen had ceased, methyl iodide (0.5 ml) was added and the mixture stirred at room temperature for 0.5 hours. Water was added and the mixture extracted with diethyl ether. The combined ether extracts were treated with 2N hydrochloric acid. The aqueous acid solution was separated, basified with solid sodium carbonate and extracted with chloroform. The combined chloroform extracts were washed with water, dried (MgSO4) and evaporated. The residue was purified by chromatography on silica and eluted with chloroform to give the title compound as a gum. This was dissolved in diethyl ether and treated with ethereal HCl to give the crystalline hydrochloride salt, 1.4 g m.p. 144°-6° C.

Workup

  1. extractionthe mixture extracted with diethyl ether
  2. additionThe combined ether extracts were treated with 2N hydrochloric acid
  3. customThe aqueous acid solution was separated
  4. extractionextracted with chloroform
  5. washThe combined chloroform extracts were washed with water
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe residue was purified by chromatography on silica
  9. washeluted with chloroform

Sources & evidence

ORD record
ord-3295edfd5a2f4302a765061039227a84
Source dataset
uspto-grants-1990_12
Patent number
US04975431

Reaction notes

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