Dimethylformamide → HCID 20394513, compound

HRID 261615Notes

Reaction equation

HRID 261615 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([CH:12]2[CH2:17][C:16]([CH3:18])=[CH:15][CH2:14][NH:13]2)([CH3:11])[CH3:10])=[CH:5][CH:4]=1.[CH2:19](I)[CH2:20][CH2:21][CH2:22][CH3:23].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH2:19]([N:13]1[CH2:14][CH:15]=[C:16]([CH3:18])[CH2:17][CH:12]1[C:9]([C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)([CH3:11])[CH3:10])[CH2:20][CH2:21][CH2:22][CH3:23]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 123351-IodopentaneHCID 20394498HCID 20394498, compound

Product 1

HCID 20394513HCID 20394513, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1,2,3,6-tetrahydro-2-[1-(4-methoxyphenyl)-1-methylethyl]-4-methylpyridine (2.9 g), pentyl iodide (2.34 g), potassium carbonate (3 g) and dimethylformamide (20 ml) was heated to reflux for 4 hours while stirring. After cooling and adding water, the reaction product was extracted with benzene. The extract was washed twice with water, dried over potassium carbonate and distilled to remove benzene to obtain 2.8 g of 1,2,3,6-tetrahydro-1-pentyl-2-[1-(4-methoxyphenyl)-1-methylethyl]-4-methylpyridine as a viscous mass. To the mass was added 20 ml of 47% hydrobromic acid and the mixture was heated to reflux for 10 hours while stirring, after cooling, made alkaline with a concentrated ammonia water under cooling and extracted with chloroform. The extract was dried over sodium sulfate and distilled to remove chloroform. The residue was fed to a column chromatograph on silica gel and eluted with chloroform. Chloroform was distilled off from the eluate to obtain 2.2 g of 1,2,3,4,5,6-hexahydro-8-hydroxy-3-pentyl- 2,6-methano-1,1,6-trimethyl-3-benzazocine as a viscous mass. The product was treated as in Example 1-(5) to obtain the corresponding hydrochloride as colorless fine needles having a melting point above 230° C. (sublimable) after the recrystallization from methanol-ethyl ether.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 hours
  3. temperatureAfter cooling
  4. extractionthe reaction product was extracted with benzene
  5. washThe extract was washed twice with water
  6. dry with materialdried over potassium carbonate
  7. distillationdistilled
  8. customto remove benzene

Sources & evidence

ORD record
ord-850d26f45ef4480f802d0e780ac4370f
Source dataset
uspto-grants-1979_08
Patent number
US04166174

Reaction notes

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