Hydrochloric Acid → 1-Phenoxycarbonyl-4-ethynyl-4-(2-nitrophenoxy)piperidine

HRID 2232326Notes

Reaction equation

HRID 2232326 reaction equation
C[N:2]1[CH2:7][CH2:6][C:5]([C:18]#[CH:19])([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N+:15]([O-:17])=[O:16])[CH2:4][CH2:3]1.Cl.[C:21]1([O:27][C:28](Cl)=[O:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>C(Cl)Cl>[O:27]([C:28]([N:2]1[CH2:3][CH2:4][C:5]([C:18]#[CH:19])([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N+:15]([O-:17])=[O:16])[CH2:6][CH2:7]1)=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 15891Phenyl chloroformateHCID 212725701-Methyl-4-ethynyl-4-(2-nitrophenoxy)piperidine

Product 1

HCID 142814851-Phenoxycarbonyl-4-ethynyl-4-(2-nitrophenoxy)piperidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-methyl-4-ethynyl-4-(2-nitrophenoxy)piperidine (liberated from 10.0 g of the hydrochloride) in 45 ml of methylene chloride was added dropwise a solution of 5.8 g of phenylchloroformate in 45 ml of methylene chloride. The mixture was stirred at room temperature for 1 hr and at reflux, under nitrogen, for 16 hrs. The solution was allowed to cool to room temperature, poured into water, extracted with methylene chloride, washed with saturated sodium chloride solution and dried over anhydrous potassium carbonate. Filtration followed by evaporation of solvent provided an oil (13.9 g). A 2.2 g sample of the oil was chromatographed on 150 g of alumina. The column was eluted with three 150 ml volume of ether. Evaporation of the solvent from the second fraction provided 1.36 g (65%) of product. Recrystallization from isopropyl alcohol provided the analytical sample, mp 76°-80°.

Workup

  1. temperatureat reflux, under nitrogen, for 16 hrs
  2. temperatureto cool to room temperature
  3. extractionextracted with methylene chloride
  4. washwashed with saturated sodium chloride solution
  5. dry with materialdried over anhydrous potassium carbonate
  6. filtrationFiltration
  7. customfollowed by evaporation of solvent

Sources & evidence

ORD record
ord-75afe45ab29d455798a2d18c2bd1c3c1
Source dataset
uspto-grants-1988_11
Patent number
US04788201

Reaction notes

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