HCID 58912940, compound → 2-[4-(4-Aminobutyl)phenoxy]-N,N-bis-(2-hydroxyethyl)acetamide

HRID 252179Notes

Reaction equation

HRID 252179 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:31])[N:24]([CH2:28][CH2:29][OH:30])[CH2:25][CH2:26][OH:27])=[CH:17][CH:16]=1)C1C=CC=CC=1.[H][H]>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]([CH2:28][CH2:29][OH:30])[CH2:25][CH2:26][OH:27])=[O:31])=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 58912940HCID 58912940, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 220544472-[4-(4-Aminobutyl)phenoxy]-N,N-bis-(2-hydroxyethyl)acetamideYield 72%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a degassed solution of [4-(4-{[N,N-bis-(2-hydroxyethyl)carbamoyl]methoxy}phenyl)-butyl]carbamic acid benzyl ester 25 (0.19 g, 0.43 mmol) in ethanol (4 mL) was added 10% palladium on activated carbon (0.1 g, 50% wet). The mixture was hydrogenated overnight at 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, 20-5:1:0.1-1 dichloromethane/methanol/concentrated ammonium hydroxide, v/v) to provide 26 (0.09 g, 72%) as a colorless oil. 1H NMR (300 MHz, CD3OD) δ 1.56 (m, 4H), 2.56 (t, 2H), 2.65 (t, 1H), 3.29 (m, 1H), 3.55 (m, 4H), 3.72 (m, 4H), 4.90 (s, 2H), 6.86 (d, 2H), 7.09 (d, 2H). m/z (ESI): 311 [C16H26N2O4+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, 20-5:1:0.1-1 dichloromethane/methanol/concentrated ammonium hydroxide, v/v)

Sources & evidence

ORD record
ord-307393e2b38c42198f095413babc9f4b
Source dataset
uspto-grants-2011_01
Patent number
US07868010B2

Reaction notes

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