Benzyl Bromide → HCID 23468804, compound

HRID 128312Notes

Reaction equation

HRID 128312 reaction equation
CS(O[CH2:6][CH2:7][CH:8]([C:16]1[CH:17]=[C:18]([Br:27])[C:19]2[O:23][C:22]([CH3:24])=[C:21]([CH3:25])[C:20]=2[CH:26]=1)[CH2:9][CH2:10]OS(C)(=O)=O)(=O)=O.C([N:30]([CH2:33][CH3:34])CC)C.C(Br)[C:36]1[CH:41]=[CH:40]C=[CH:38][CH:37]=1>O1CCCC1>[CH2:33]([N:30]1[CH2:10][CH2:9][CH:8]([C:16]2[CH:17]=[C:18]([Br:27])[C:19]3[O:23][C:22]([CH3:24])=[C:21]([CH3:25])[C:20]=3[CH:26]=2)[CH2:7][CH2:6]1)[C:34]1[CH:40]=[CH:41][CH:36]=[CH:37][CH:38]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 23468930HCID 23468930, compound

Product 1

HCID 23468804HCID 23468804, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The starting material is prepared as follows: (a) 3.08 g (0.01 mol) of 4-(2,3-dimethyl-7-bromo-5-benzofuranyl)-piperidine (c.f. Example 21) are dissolved in 100 ml of tetrahydrofuran, and 1.4 ml of triethylamine and then 1.30 ml (0.0105 mol) of benzyl bromide are added to the solution. A white precipitate thereby forms. The reaction mixture is stirred at room temperature for 31/2 hours. The solvent and excess triethylamine are then removed under a waterpump vacuum and the residue is added to water. The mixture is extracted 3 times with ether and the combined ether solutions are washed once with 2 N sodium hydroxide solution and then twice with water and once with saturated sodium chloride solution. The combined ether solutions are then dried over sodium sulfate and evaporated completely under a waterpump vacuum. 1-Benzyl-4-(2,3-dimethyl-7-bromo-5-benzofuranyl)-piperidine which melts at 86°-91°, is thereby obtained. In the thin layer chromatogram on silica gel using chloroform/5% methanol as the running agent, this product has an Rf value of 0.4. A sample recrystallised from ether/hexane has a melting point of 88°-91°. The product is of sufficient purity for further use.

Workup

  1. customThe starting material is prepared
  2. customThe solvent and excess triethylamine are then removed under a waterpump vacuum
  3. additionthe residue is added to water
  4. extractionThe mixture is extracted 3 times with ether
  5. washthe combined ether solutions are washed once with 2 N sodium hydroxide solution
  6. dry with materialThe combined ether solutions are then dried over sodium sulfate
  7. customevaporated completely under a waterpump vacuum

Sources & evidence

ORD record
ord-e3a6cafc8780445495b4ded83b3090fa
Source dataset
uspto-grants-1981_03
Patent number
US04259338

Reaction notes

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