Sodium Hydroxide → 5-Benzyl-4,5,6,7-tetrahydro-furo[3,2-c]pyridine

HRID 2301102Notes

Reaction equation

HRID 2301102 reaction equation
Cl[CH2:2][CH2:3][N:4]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:5][C:6]1[CH:10]=[CH:9][O:8][CH:7]=1.CCCCCC.C([Li])CCC.[OH-].[Na+]>O1CCCC1>[CH2:11]([N:4]1[CH2:3][CH2:2][C:7]2[O:8][CH:9]=[CH:10][C:6]=2[CH2:5]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 18377420N-benzyl-N-(3-furylmethyl)-2-chloroethylamineHCID 178418244HCID 178418244, compound

Product 1

HCID 183773045-Benzyl-4,5,6,7-tetrahydro-furo[3,2-c]pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2-(Benzyl-(3-furylmethyl)amino)ethanol (6.5 g, 28 mmol), triethylamine (5.9 ml, 42 mmol), 4-dimethylaminopyridine (250 mg, 2.1 mmol) and tosyl chloride (6.4 g, 34 mmol) were stirred at room temperature for 17 hours in dichloromethane (260 ml). The reaction solution was mixed with dichloromethane, washed with water and saturated brine and then dried with anhydrous magnesium sulfate. The solvent was removed by evaporation from the organic layer under a reduced pressure, and the thus obtained material was separated and purified by a silica gel column chromatography to obtain 5.4 g of crude 1-chloro-2-(benzyl-(3-furylmethyl)amino)ethane. The crude 1-chloro-2-(benzyl-(3-furylmethyl)amino)ethane (1.8 g) was dissolved in anhydrous tetrahydrofuran (35 ml) and cooled to 0° C. In an atmosphere of argon, n-butyl lithium hexane solution (14 mmol) was added thereto to carry out 2 hours of the reaction at room temperature. The reaction solution was mixed with 1 N sodium hydroxide aqueous solution, the reaction product was extracted with dichloromethane, and then the organic layer was washed with saturated brine and dried with anhydrous magnesium sulfate. The solvent was removed by evaporation from the organic layer under a reduced pressure, and the thus obtained material was separated and purified by a silica gel column chromatography to obtain 1.1 g (5.1 mmol, 73% in yield) of the title compound.

Workup

  1. customto carry out 2 hours of the reaction at room temperature
  2. extractionthe reaction product was extracted with dichloromethane
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customThe solvent was removed by evaporation from the organic layer under a reduced pressure
  6. customthe thus obtained material was separated
  7. custompurified by a silica gel column chromatography
  8. customto obtain

Sources & evidence

ORD record
ord-74c4d472cf414d6990de5cfcdad30e7d
Source dataset
uspto-grants-2002_12
Patent number
US06498251B1

Reaction notes

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