Phenylacetic Acid → 2-phenyl-N-propylacetamide

HRID 2421639Notes

Reaction equation

HRID 2421639 reaction equation
CCN=C=[N:5][CH2:6][CH2:7][CH2:8]N(C)C.Cl.[C:13]1([CH2:19][C:20]([OH:22])=O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N)CC.C1C=CC2N(O)N=NC=2C=1>CC#N.CCOC(C)=O>[C:13]1([CH2:19][C:20]([NH:5][CH2:6][CH2:7][CH3:8])=[O:22])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 999Phenylacetic AcidHCID 7852PropylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 31133702-phenyl-N-propylacetamide

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

EDAC.HCl (959 mg, 5 mmol) was added to a mixture of phenylacetic acid (681 mg, 5 mmol), propylamine (411 μL, 5 mmol) and HOBT (676 mg, 5 mmol) in 5 mL of CH3CN. The reaction was stirred for 72 hours. After this time, the mixture was diluted with AcOEt. The organic layer was washed three times with HCl 2N, three times with NaOH 2N, dried over MgSO4 and concentrated. A with solid was obtained (576 mg, 65%). NMR 1H (ppm, CDCl3): 7.39-7.24 (m, 5H), 5.38 (br. s., 1H), 3.57 (s, 2H), 3.20-3.13 (m, 2H), 1.45 (sex. J3=7.19 Hz, 2H), 0.83 (t, J3=7.40 Hz, 3H).

Workup

  1. washThe organic layer was washed three times with HCl 2N, three times with NaOH 2N
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customA with solid was obtained (576 mg, 65%)

Sources & evidence

ORD record
ord-a4f2a6a8ba0a41ab845b857266c8eee8
Source dataset
uspto-grants-2011_06
Patent number
US07956216B2

Reaction notes

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