Hydrochloric Acid → HCID 86608806, compound

HRID 1987764Notes

Reaction equation

HRID 1987764 reaction equation
[N+:1]([C:4]1[CH:31]([CH3:32])[CH:8]2[CH2:9][C:10]([CH2:13][C:14]3[CH2:15][CH2:16][N:17]([C:20]4[CH:25]=[CH:24][C:23]([N:26]5[CH:30]=[CH:29][N:28]=[CH:27]5)=[CH:22][CH:21]=4)[CH2:18][CH:19]=3)([CH3:12])[O:11][C:7]2=[C:6]([CH3:33])[C:5]=1[CH3:34])([O-])=O.C(O)C.Cl.[OH-].[Na+]>O>[NH2:1][C:4]1[CH:31]([CH3:32])[CH:8]2[CH2:9][C:10]([CH2:13][C:14]3[CH2:19][CH2:18][N:17]([C:20]4[CH:21]=[CH:22][C:23]([N:26]5[CH:30]=[CH:29][N:28]=[CH:27]5)=[CH:24][CH:25]=4)[CH2:16][CH:15]=3)([CH3:12])[O:11][C:7]2=[C:6]([CH3:33])[C:5]=1[CH3:34]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 86608807HCID 86608807, compound

Product 1

HCID 86608806HCID 86608806, compoundYield 82.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 1.2 g of 4-(±)-(5-nitro-2,4,6,7-tetramethyldihydrobenzofuran-2-ylmethyl)-1-(4-imidazol-1-ylphenyl)-1,2,3,6-tetrahydropyridine, 30 ml of ethanol was added and 3.6 g of stannous chloride-dihydrate and 15 ml of concentrated hydrochloric acid were added, followed by heating at reflux for 8 hours. The reaction solution was poured into water, neutralized with a 1N sodium hydroxide solution and then extracted with chloroform. The organic layer was washed with saturated saline and then dried over anhydrous magnesium sulfate. After removing magnesium sulfate by filtration and concentrating under reduced pressure, the residue was subjected to silica gel column chromatography (chloroform:methanol=20:1) to obtain 0.93 g of the objective product (mp: 161-163° C.).

Workup

  1. temperatureby heating
  2. temperatureat reflux for 8 hours
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customAfter removing magnesium sulfate
  7. filtrationby filtration
  8. concentrationconcentrating under reduced pressure

Sources & evidence

ORD record
ord-d64daa6aebca4e7a879f398cfe2f72cc
Source dataset
uspto-grants-2009_06
Patent number
US07553837B2

Reaction notes

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