HCID 21031127, compound → 2-[4-(4-aminobutyl)phenoxy]-N,N-dimethylacetamide

HRID 1971058Notes

Reaction equation

HRID 1971058 reaction equation
C(OC(=O)[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23](=[O:27])[N:24]([CH3:26])[CH3:25])=[CH:17][CH:16]=1)C1C=CC=CC=1>C(O)C.[Pd]>[NH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]([N:24]([CH3:25])[CH3:26])=[O:27])=[CH:17][CH:16]=1

Participants

4

Reactant 1

HCID 21031127HCID 21031127, compound

Product 1

HCID 220544312-[4-(4-aminobutyl)phenoxy]-N,N-dimethylacetamideYield 60%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a degassed solution of [4-(4-dimethylcarbamoylmethoxyphenyl)butyl]carbamic acid benzyl ester (28) (0.26 g, 0.68 mmol) in ethanol (10 mL) was added 10% palladium on activated carbon (0.1 g, 50% wet). The mixture was stirred at room temperature overnight under atmospheric hydrogen. The catalyst was filtered through a pad of diatomaceous earth and the solvent was evaporated in vacuo. The residue was purified by flash chromatography (silica gel, dichloromethane/methanol/concentrated ammonium hydroxide, 100:5:1, v/v) to provide 2-[4-(4-aminobutyl)phenoxy]-N,N-dimethylacetamide 29 (100 mg, 60% yield) as a white solid. 1H NMR (300 MHz, CD3OD) δ 1.55 (m, 4H), 2.55 (m, 2H), 2.66 (m, 2H), 2.90 (s, 3H), 3.05 (s, 3H), 4.70 (s, 2H), 6.80 (d, 2H), 7.05 (d, 2H). m/z (ESI): 251 [C14H22N2O2+H]+.

Workup

  1. filtrationThe catalyst was filtered through a pad of diatomaceous earth
  2. customthe solvent was evaporated in vacuo
  3. customThe residue was purified by flash chromatography (silica gel, dichloromethane/methanol/concentrated ammonium hydroxide, 100:5:1

Sources & evidence

ORD record
ord-8be95de3de28455aa021612b130227ba
Source dataset
uspto-grants-2013_04
Patent number
US08431579B2

Reaction notes

Loading…