O-Methylhydroxylamine hydrochloride → 1-Metyl-3-methoxyiminomethyl-4-(3,4-dichlorophenyl)piperidine

HRID 843267Notes

Reaction equation

HRID 843267 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=2)[CH:4]([CH:16]=O)[CH2:3]1.Cl.[O:19]([NH2:21])[CH3:20]>C(O)(C)C>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=2)[CH:4]([CH:16]=[N:21][O:19][CH3:20])[CH2:3]1

Participants

4

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 22617036HCID 22617036, compound

Product 1

HCID 850740351-Metyl-3-methoxyiminomethyl-4-(3,4-dichlorophenyl)piperidineYield 40.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 1-methyl-3-formyl-4-(3,4-dichlorophenyl)piperidine (10 g, 33 mmol) in warm isopropanol (100 mL) was added methoxylamine hydrochloride (3 g, 36 mmol). The reaction was heated at reflux for 30 min. The solvent was evaporated off and the residue made basic (pH=9) using concentrated ammonia. Extraction with ether afforded 8.5 g of crude product. Purification by repeated column chromatography on silica using EtOAc/Et3N (95:5) as eleuent afforded 4 g of the title compound as an oil.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 30 min
  3. customThe solvent was evaporated off
  4. extractionExtraction with ether
  5. customafforded 8.5 g of crude product
  6. customPurification

Sources & evidence

ORD record
ord-ae17b915266a403fbfa97832321d1d04
Source dataset
uspto-grants-2002_04
Patent number
US06376673B1

Reaction notes

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