Triethylamine → 6-(6-Phenylhexyl)-4,5,6,7-tetrahydrofuro[2,3-c]pyridine

HRID 611073Notes

Reaction equation

HRID 611073 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.Cl.[O:22]1[C:26]2[CH2:27][NH:28][CH2:29][CH2:30][C:25]=2[CH:24]=[CH:23]1>CCOCC.CS(Cl)(=O)=O>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:28]2[CH2:29][CH2:30][C:25]3[CH:24]=[CH:23][O:22][C:26]=3[CH2:27]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 8471Triethylamine2×HCID 5201106-Phenyl-1-hexanolHCID 195999074,5,6,7-Tetrahydrofuro[2,3-c]pyridine hydrochloride

Product 1

HCID 154293296-(6-Phenylhexyl)-4,5,6,7-tetrahydrofuro[2,3-c]pyridine

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 31297Methanesulfonyl chlorideSolvent

Procedure

To a solution of 0.39 g (2.2 mmol) of 6-phenylhexan-1-ol and 0.38 ml (2.7 mmol) of triethylamine in 20 ml of ether, methanesulfonyl chloride was added dropwise under ice-cooling, followed by stirring for 10 minutes. The ether solution was washed with water and saturated aqueous sodium chloride, after which it was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The residual oil (crude 6-phenylhexyl methanesulfonate) was dissolved in 30 ml of acetonitrile; 0.289 g (1.811 mmol) of 4,5,6,7-tetrahydrofuro[2,3-c]pyridine hydrochloride and 0.76 ml (5.4 mmol) of triethylamine were added, followed by refluxing for 3 hours. The solvent was distilled off from the reaction mixture under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=6/1) to yield the desired product.

Workup

  1. temperaturecooling
  2. washThe ether solution was washed with water and saturated aqueous sodium chloride
  3. dry with materialafter which it was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. dissolutionThe residual oil (crude 6-phenylhexyl methanesulfonate) was dissolved in 30 ml of acetonitrile
  6. temperatureby refluxing for 3 hours
  7. distillationThe solvent was distilled off from the reaction mixture under reduced pressure
  8. customThe resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=6/1)

Sources & evidence

ORD record
ord-691fe254c0b54557afd3865fd86e4459
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

Loading…