Acetic Acid → 2-[4-(4-Aminobutyl)phenoxy]-N-phenylacetamide

HRID 1971051Notes

Reaction equation

HRID 1971051 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])[NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:17][CH:16]=1)C1C=CC=CC=1.C(O)(=O)C>C(O)C.C1COCC1.[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]([NH:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:31])=[CH:17][CH:16]=1

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 21031125[4-(4-Phenylcarbamoylmethoxyphenyl)butyl]carbamic acid benzyl ester

Product 1

HCID 220544372-[4-(4-Aminobutyl)phenoxy]-N-phenylacetamideYield 97.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of [4-(4-phenylcarbamoylmethoxyphenyl)butyl]carbamic acid benzyl ester 18 (0.30 g, 0.69 mmol) in ethanol (10 mL), THF (6 mL), and acetic acid (2 mL) was stirred at room temperature for 2 h under hydrogen atmosphere in the presence of 10% Pd/C catalyst (0.2 g, 50% wet). The catalyst was removed by suction filtration and the filtrate was concentrated in vacuo. The residue was purified by flash silica gel column chromatography eluting with CH2Cl2/methanol/concentrated ammonium hydroxide (30:1:0, 30:1:0.3, v/v) to give the desired amine 19 as a white solid (200 mg, 97% yield). 1H NMR (300 MHz, CD3OD) δ 1.60 (m, 4H), 2.55 (m, 2H), 2.70 (m, 2H), 4.60 (s, 2H), 6.88 (d, 2H), 7.15 (m, 3H), 7.35 (m, 2H), 7.58 (d, 2H), 8.25 (s, 1H). m/z (ESI): 299 [C18H22N2O2+H]+.

Workup

  1. customThe catalyst was removed by suction filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by flash silica gel column chromatography
  4. washeluting with CH2Cl2/methanol/concentrated ammonium hydroxide (30:1:0, 30:1:0.3

Sources & evidence

ORD record
ord-da102940a54d4f0287a86af8bd783d31
Source dataset
uspto-grants-2013_04
Patent number
US08431579B2

Reaction notes

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