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

HRID 611079Notes

Reaction equation

HRID 611079 reaction equation
Cl[CH2:2][CH2:3][N:4]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:5][C:6]1[CH:10]=[CH:9][O:8][CH:7]=1.C([Li])CCC.[OH-].[Na+]>O1CCCC1.CCCCCC>[C:17]1([CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][N:4]2[CH2:3][CH2:2][C:7]3[O:8][CH:9]=[CH:10][C:6]=3[CH2:5]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 19599937N-(2-chloroethyl)-N-(3-furylmethyl)-6-phenylhexylamineHCID 178418339Butyllithium

Product 1

HCID 195999645-(6-Phenylhexyl)-4,5,6,7-tetrahydrofuro[3,2-c]pyridine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of 1.533 g (4.793 mmol) of N-(2-chloroethyl)-N-(3-furylmethyl)-6-phenylhexylamine in 100 ml of tetrahydrofuran, 8.99 ml (14.4 mmol) of 1.6 M n-butyl lithium in hexane was added under ice-cooling, followed by stirring at room temperature for 4 hours. This 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 the desired product.

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-23b746b762c74e78ab1e67513951122c
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

Loading…