Hydrochloric Acid → 1-Methyl-4-(2-aminophenoxy)-4-ethynylpiperidine

HRID 1193549Notes

Reaction equation

HRID 1193549 reaction equation
[CH3:1][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-])=O)[CH2:4][CH2:3]1.Cl.CO.C(=O)([O-])[O-].[Na+].[Na+]>CCOCC.[Fe].O>[CH3:1][N:2]1[CH2:3][CH2:4][C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH2:15])([C:18]#[CH:19])[CH2:6][CH2:7]1

Participants

8

Reactant 4

HCID 313Hydrochloric Acid2×HCID 887MethanolHCID 10340Sodium CarbonateHCID 212725701-Methyl-4-ethynyl-4-(2-nitrophenoxy)piperidine

Product 1

HCID 212725921-Methyl-4-(2-aminophenoxy)-4-ethynylpiperidineYield 83%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A suspension of 1-methyl-4-ethynyl-4-(2-nitrophenoxy)piperidine (liberated from 10.0 g of the hydrochloride), 140 ml of methanol, 40 ml of water, 10 ml of conc hydrochloric acid and 20 g of iron (reduced electroytic) was stirred for 0.5 hr at 45° under nitrogen. The mixture was allowed to cool to room temperature, poured into saturated sodium carbonate solution, extracted twice with ether; dried over anhydrous potassium carbonate, filtered, and the solvent was evaporated to provide an oil. The oil was dissolved in ether. Precipitation with ethereal hydrogen chloride provided 8.59 g (83%) of product. Recrystallization from ethanol provided the analytical sample.

Workup

  1. extractionextracted twice with ether
  2. dry with materialdried over anhydrous potassium carbonate
  3. filtrationfiltered
  4. customthe solvent was evaporated
  5. customto provide an oil
  6. customPrecipitation with ethereal hydrogen chloride

Sources & evidence

ORD record
ord-1d73c2702d7149f5b6c0e1fa472ed935
Source dataset
uspto-grants-1989_03
Patent number
US04810792

Reaction notes

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