Hydrochloric Acid → N-[4-(3-methoxyamino-propyl)-phenyl]-acetamide

HRID 2236955Notes

Reaction equation

HRID 2236955 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH:13]=O)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].Cl.[O:16]([NH2:18])[CH3:17].B.Cl>CO.N1C=CC=CC=1>[CH3:17][O:16][NH:18][CH2:13][CH2:12][CH2:11][C:8]1[CH:7]=[CH:6][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 521874O-Methylhydroxylamine hydrochlorideHCID 99206073-(4-Acetamidophenyl)propanal

Product 1

HCID 86619588N-[4-(3-methoxyamino-propyl)-phenyl]-acetamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 1049PyridineSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3-(4-acetamidophenyl)propanal (96 mg, 0.50 mmol), methoxylamine hydrochloride (92 mg, 1.1 mmol), and pyridine (110 μL) in methanol (0.7 mL) is heated in a 70° C. oil bath for 18 hours and then allowed to cool to room temperature. Methanol (1 mL) is added and the mixture is cooled to 0° C. in an ice-water bath. Borane.pyridine complex (0.11 mL, 1.1 mmol) is added, followed by the dropwise addition of 10% aqueous hydrochloric acid. The mixture is allowed to warm to room temperature and then concentrated under reduced pressure. The residue is purified by reverse-phase HPLC to give N-[4-(3-methoxyamino-propyl)-phenyl]-acetamide.

Workup

  1. temperatureto cool to room temperature
  2. temperaturethe mixture is cooled to 0° C. in an ice-water bath
  3. additionpyridine complex (0.11 mL, 1.1 mmol) is added
  4. temperatureto warm to room temperature
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by reverse-phase HPLC

Sources & evidence

ORD record
ord-b8df1eb0b0ba412a97bc884570706e00
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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