Hydrochloric Acid → HCID 14281498, compound

HRID 1193555Notes

Reaction equation

HRID 1193555 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][C:7]([C:21]#[CH:22])([O:10][C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=2[N+:18]([O-])=O)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].CO.[ClH:25].C(=O)([O-])[O-].[Na+].[Na+]>O.[Fe]>[ClH:25].[C:1]([N:4]1[CH2:9][CH2:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=2[NH2:18])([C:21]#[CH:22])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 10340Sodium CarbonateHCID 14281494HCID 14281494, compound

Product 1

HCID 14281498HCID 14281498, compoundYield 17.7%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

To a stirred solution of 3.14 g of 1-acetyl-4-ethynyl-4-(4-fluoro-2-nitrophenoxy)piperidine and 42 ml of methanol was added a solution of 3 ml of concentrated hydrochloric acid in 12 ml water. To the stirred mixture in a water bath was added 6.1 g of iron (powdered electrolytic) The mixture was stirred for 1 hr, poured into ice, made basic by the addition of sodium carbonate solution, extracted twice with methylene chloride and washed with saturated sodium chloride solution. The mixture was dried over anhydrous potassium carbonate, filtered and the solvent evaporated to provide an oil. The oil was purified on a Waters Prep 500 High Pressure Liquid Chromatograph instrument, using a silica gel column and eluting with 2% methanol/dichloromethane. The appropriate fractions were evaporated and the residue was treated with ethereal hydrogen chloride to provide 0.57 g (17.7%) of product, mp 206°-208°, after recrystallization from ethanol/methanol.

Workup

  1. additionpoured into ice
  2. extractionextracted twice with methylene chloride
  3. washwashed with saturated sodium chloride solution
  4. dry with materialThe mixture was dried over anhydrous potassium carbonate
  5. filtrationfiltered
  6. customthe solvent evaporated
  7. customto provide an oil
  8. customThe oil was purified on a Waters Prep 500 High Pressure Liquid Chromatograph instrument
  9. washeluting with 2% methanol/dichloromethane
  10. customThe appropriate fractions were evaporated
  11. additionthe residue was treated with ethereal hydrogen chloride

Sources & evidence

ORD record
ord-3986e3a921b04ba1bcd275e8de89bb12
Source dataset
uspto-grants-1989_03
Patent number
US04810792

Reaction notes

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