Furan, 2-(bromomethyl)tetrahydro- → HCID 20355892, compound

HRID 371723Notes

Reaction equation

HRID 371723 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][CH:8]2[CH:13]([CH3:14])[C:12]([CH3:16])([OH:15])[CH2:11][CH2:10][NH:9]2)=[CH:5][CH:4]=1.C(=O)(O)[O-].[Na+].[CH2:24](Br)[CH:25]1[O:29][CH2:28][CH2:27][CH2:26]1>CN(C)C=O>[CH2:24]([N:9]1[CH2:10][CH2:11][C:12]([CH3:16])([OH:15])[CH:13]([CH3:14])[CH:8]1[CH2:7][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:18][CH:17]=1)[CH:25]1[O:29][CH2:28][CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 14501Furan, 2-(bromomethyl)tetrahydro-HCID 516892Sodium BicarbonateHCID 21822921HCID 21822921, compound

Product 1

HCID 20355892HCID 20355892, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

24.9 gm (0.1 mol) of 2-(p-methoxybenzyl)-3,4-dimethyl-4-hydroxy-piperidine were stirred in 200 ml of dimethylformamide in the presence of 12.6 gm of sodium bicarbonate for 24 hours at 100° C with 19.7 gm (0.12 mol) of tetrahydrofurfuryl bromide. Subsequently, the reaction mixture was evaporated in vacuo, and the residue shaken with a mixture of 150 ml of chloroform and 100 ml of water. After isolation in a separating funnel, the aqueous phase was extracted once more with 50 ml of chloroform. The combined chloroform extracts were washed with water, dried with sodium sulfate and evaporated in vacuo. In analogy to the procedure described in Example 1, the residue was purified by column-chromatography on aluminum oxide (700 gm, activity stage III, neutral), using chloroform as the flow agent. After evaporation of the combined eluates comprising the pure product, a residue of 16 gm was obtained, which was further reacted as such in the following step.

Workup

  1. customSubsequently, the reaction mixture was evaporated in vacuo
  2. extractionAfter isolation in a separating funnel, the aqueous phase was extracted once more with 50 ml of chloroform
  3. washThe combined chloroform extracts were washed with water
  4. dry with materialdried with sodium sulfate
  5. customevaporated in vacuo
  6. customthe residue was purified by column-chromatography on aluminum oxide (700 gm, activity stage III, neutral)
  7. customAfter evaporation of the combined eluates
  8. customa residue of 16 gm was obtained
  9. customwhich was further reacted as such in the following step

Sources & evidence

ORD record
ord-0e3597aa8d1d4a8bb5cc72380f0eefc7
Source dataset
uspto-grants-1978_05
Patent number
US04087532

Reaction notes

Loading…