Hydrochloric Acid → HCID 69838142, compound

HRID 1585401Notes

Reaction equation

HRID 1585401 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:10]1([C:16]2[O:21][C:20](=[O:22])[CH2:19][CH2:18][CH:17]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(OCC)(=O)C.Cl>C1(C)C=CC=CC=1>[CH2:3]([N:2]([CH3:1])[C:20](=[O:22])[CH2:19][CH2:18][CH2:17][C:16](=[O:21])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7669N-MethylbenzylamineHCID 8857Ethyl AcetateHCID 12424833HCID 12424833, compound

Product 1

HCID 69838142HCID 69838142, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The 5-oxo-5-phenylpentanoic acid benzyl-methyl amide was prepared by refluxing N-methylbenzylamine (10.5 mmol) and 6-phenyl-3,4-dihydro-pyran-2-one (10.5 mmol) in toluene for one hour. The reaction was allowed to stir overnight at room temperature. It was poured into 100 mL of ethyl acetate and 100 mL of 1N HCl. The organic extracts were washed with 100 mL of 1N NaOH, 100 mL of water and dried over MgSO4. The crude product was flash chromatographed (CH2Cl2 /MeOH 98/2) to afford a liquid. 1H NMR (CDCl3) δ 2.0-2.2 (m, 2 H), 2.5 (t, 2 H), 2.93/2.96 (s/s, 3 H), 3.0-3.2 (m, 2 H), 4.5/4.6 (s/s, 2 H), 7.1-7.6 (m, 8 H), 7.8-8.0 (m, 2 H).

Workup

  1. washThe organic extracts were washed with 100 mL of 1N NaOH, 100 mL of water
  2. dry with materialdried over MgSO4
  3. customchromatographed (CH2Cl2 /MeOH 98/2)
  4. customto afford a liquid

Sources & evidence

ORD record
ord-3ada12920db74c8fb207cc588fc651df
Source dataset
uspto-grants-1999_08
Patent number
US05936128

Reaction notes

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