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

HRID 611062Notes

Reaction equation

HRID 611062 reaction equation
[CH2:1]([N:8]([CH2:15][CH2:16]Cl)[CH2:9][C:10]1[CH:14]=[CH:13][O:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[OH-].[Na+]>O1CCCC1.CCCCCC>[CH2:1]([N:8]1[CH2:15][CH2:16][C:11]2[O:12][CH:13]=[CH:14][C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 18377420N-benzyl-N-(3-furylmethyl)-2-chloroethylamineHCID 178418339Butyllithium

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of 0.209 g (0.837 mmol) of N-benzyl-N-(3-furylmethyl)-2-chloroethylamine in 50 ml of tetrahydrofuran, 1.05 ml (1.67 mmol) of 1.6 M n-butyl lithium in hexane was added under ice-cooling, followed by stirring at room temperature for 2 hours. The reaction mixture was poured into aqueous sodium hydroxide and extracted with dichloromethane 3 times. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=9/1) to yield 5-benzyl-4,5,6,7-tetrahydrofuro[3,2-c]pyridine.

Workup

  1. temperaturecooling
  2. extractionextracted with dichloromethane 3 times
  3. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-02046e70fcf04cef84e72d54423d3a1d
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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