Propionyl chloride → N-(2-(4-Phenoxyphenyl)ethyl)propionamide

HRID 1781161Notes

Reaction equation

HRID 1781161 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][NH2:16])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17](Cl)(=[O:20])[CH2:18][CH3:19]>C(Cl)Cl.N1C=CC=CC=1.C(OCC)(=O)C>[O:1]([C:8]1[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][NH:16][C:17](=[O:20])[CH2:18][CH3:19])=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 62324Propionyl chlorideHCID 1455354-Phenoxyphenethylamine

Product 1

HCID 19048230N-(2-(4-Phenoxyphenyl)ethyl)propionamide

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the solution of crude amine resulting from Example 67E in methylene chloride (20 mL) and pyridine (5 mL) was added propionyl chloride (3.0 mL, 34 mmol). After 6 hours, the reaction was diluted with ethyl acetate (80 mL), washed with water (20 mL), 10% aqueous hydrochloric acid (20 mL), water (20 mL), saturated copper sulfate (20 mL) and brine (20 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified by column chromatography eluting with 50% ethyl acetate in hexane to give the desired product (1.23 g, 27% for the last 4 steps). 1H NMR (300 MHz, CDCl3) δ 7.36-6.95 (m, 9 H), 5.46 (bs, 1 H), 3.51 (q, 2 H), 2.80 (t, 2 H), 2.19 (q, 2 H), 1.15 (t, 3 H).

Workup

  1. washwashed with water (20 mL), 10% aqueous hydrochloric acid (20 mL), water (20 mL), saturated copper sulfate (20 mL) and brine (20 mL)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography
  6. washeluting with 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-77770289c7dd46c3b7cbc1fbd1ef978e
Source dataset
uspto-grants-1997_05
Patent number
US05631401

Reaction notes

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