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

HRID 2236736Notes

Reaction equation

HRID 2236736 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].[N:15]1C=CC=CC=1.B.Cl.[CH3:23][OH:24]>>[CH3:23][O:24][NH:15][CH2:13][CH2:12][CH2:11][C:8]1[CH:9]=[CH:10][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[CH:6][CH:7]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 887Methanol2×HCID 1049PyridineHCID 6331BoraneHCID 99206073-(4-Acetamidophenyl)propanal

Product 1

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

Conditions

Temperature
70 °C

Procedure

A mixture of 3-(4-acetamidophenyl)propanal (96 mg, 0.50 mmol), methoxy]amine 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-969d9b5703324d159300f993b227c9ce
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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