Ethyl chloroformate → 1-Ethoxycarbonyl-4-ethynyl-4-(4-fluoro-2-nitrophenoxy)piperidine

HRID 1193551Notes

Reaction equation

HRID 1193551 reaction equation
C[N:2]1[CH2:7][CH2:6][C:5]([C:19]#[CH:20])([O:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=2[N+:16]([O-:18])=[O:17])[CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].Cl[C:28]([O:30][CH2:31][CH3:32])=[O:29]>C1C=CC=CC=1>[CH2:31]([O:30][C:28]([N:2]1[CH2:7][CH2:6][C:5]([C:19]#[CH:20])([O:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=2[N+:16]([O-:18])=[O:17])[CH2:4][CH2:3]1)=[O:29])[CH3:32]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 14281483N-Methyl-4-ethynyl-4-(4-fluoro-2-nitrophenoxy)piperidine

Product 1

HCID 142814841-Ethoxycarbonyl-4-ethynyl-4-(4-fluoro-2-nitrophenoxy)piperidineYield 83.9%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A suspension of 223 g of N-methyl-4-ethynyl-4-(4-fluoro-2-nitrophenoxy)piperidine, 2 l of dry benzene, 165 g of anhydrous potassium carbonate and 130.3 g of ethyl chloroformate was stirred at reflux for 18 hr under nitrogen. The mixture was filtered and the solvent evaporated. The residue was dissolved in ether, washed with hydrochloric acid, saturated sodium bicarbonate solution, water and saturated sodium chloride solution. The ether solution was dried over anhydrous sodium sulfate and filtered. Evaporation of solvent provided an oil, which was dried at 50°-55° (1 mm). The oil crystallized to provide 226 g (83.8%) of product, mp 56°-68°.

Workup

  1. temperatureat reflux for 18 hr under nitrogen
  2. filtrationThe mixture was filtered
  3. customthe solvent evaporated
  4. dissolutionThe residue was dissolved in ether
  5. washwashed with hydrochloric acid, saturated sodium bicarbonate solution, water and saturated sodium chloride solution
  6. dry with materialThe ether solution was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customEvaporation of solvent
  9. customprovided an oil, which
  10. customwas dried at 50°-55° (1 mm)
  11. customThe oil crystallized

Sources & evidence

ORD record
ord-a6ecdb2cdda444788afe8d7659f403d1
Source dataset
uspto-grants-1989_03
Patent number
US04810792

Reaction notes

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