Methanol → 4-Ethynyl-4-(2-nitrophenoxy)piperidine maleate

HRID 2232327Notes

Reaction equation

HRID 2232327 reaction equation
O(C([N:10]1[CH2:15][CH2:14][C:13]([C:26]#[CH:27])([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[N+:23]([O-:25])=[O:24])[CH2:12][CH2:11]1)=O)C1C=CC=CC=1.CO.[OH-].[Na+].[C:32]([OH:39])(=[O:38])/[CH:33]=[CH:34]\[C:35]([OH:37])=[O:36]>O>[C:32]([OH:39])(=[O:38])/[CH:33]=[CH:34]\[C:35]([OH:37])=[O:36].[C:26]([C:13]1([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[N+:23]([O-:25])=[O:24])[CH2:14][CH2:15][NH:10][CH2:11][CH2:12]1)#[CH:27]

Participants

6

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 444266Maleic AcidHCID 142814851-Phenoxycarbonyl-4-ethynyl-4-(2-nitrophenoxy)piperidine

Product 1

HCID 142814874-Ethynyl-4-(2-nitrophenoxy)piperidine maleateYield 43%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 1.00 g of 1-phenoxycarbonyl-4-ethynyl-4-(2-nitrophenoxy)piperidine, 14 ml of methanol, and 6 ml of 15% sodium hydroxide solution was heated at reflux for 2.5 hrs under nitrogen and allowed to cool to room temperature. The mixture was poured into water, extracted twice with chloroform, washed with saturated sodium chloride solution and dried over anhydrous potassium carbonate. Evaporation of solvent provided an oil. Treatment of a solution of the oil which ethereal maleic acid provided 0.43 g (43%) of product, mp 155°-157°.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2.5 hrs under nitrogen
  3. extractionextracted twice with chloroform
  4. washwashed with saturated sodium chloride solution
  5. dry with materialdried over anhydrous potassium carbonate
  6. customEvaporation of solvent
  7. customprovided an oil

Sources & evidence

ORD record
ord-5dc3dff8b0524d5181fc0bf225e54621
Source dataset
uspto-grants-1988_11
Patent number
US04788201

Reaction notes

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