N-[2-(4-Fluoro-3-methoxyphenyl)-2-hydroxyethyl]propanamide → HCID 57440686, compound

HRID 2102344Notes

Reaction equation

HRID 2102344 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:15])[CH2:9][NH:10][C:11](=O)[CH2:12][CH3:13])=[CH:4][C:3]=1[O:16][CH3:17]>Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:15])[CH2:9][NH:10][CH2:11][CH2:12][CH3:13])=[CH:4][C:3]=1[O:16][CH3:17]

Participants

3

Reactant 1

HCID 59645261N-[2-(4-Fluoro-3-methoxyphenyl)-2-hydroxyethyl]propanamide

Product 1

HCID 57440686HCID 57440686, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Prepared following the same method as for example 3 starting with the amide from example 18 (585 mg, 2.42 mmol). After refluxing in 6M HCl (aq) the reaction mixture was cooled and extracted with diethyl ether (2×50 ml). The organic layers were discarded and the aqueous layer basified by the addition of potassium carbonate. The aqueous residue was then extracted with ethyl acetate (3×50 ml). The organic extracts were combined and dried over anhydrous magnesium sulphate, filtered and concentrated in vacuo to give the title compound as a pale yellow oil (448 mg, 1.97 mmol, 81%), 1H NMR (CD3OD, 400 MHz) δ: 0.96 (t, 3H), 1.58 (m, 2H), 2.63 (m, 2H), 2.79 (d, 2H), 3.96 (s, 3H), 4.77 (t, 1H), 6.90 (m, 1H), 7.03 (t, 1H), 7.11 (d, 1H). LRMS: m/z 228 (M-H+).

Workup

  1. customPrepared
  2. temperaturewas cooled
  3. extractionextracted with diethyl ether (2×50 ml)
  4. additionthe aqueous layer basified by the addition of potassium carbonate
  5. extractionThe aqueous residue was then extracted with ethyl acetate (3×50 ml)
  6. dry with materialdried over anhydrous magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d5e1d3bcd613426c85a54bd4e86e9c4c
Source dataset
uspto-grants-2009_08
Patent number
US07576081B2

Reaction notes

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