N-Methylbenzylamine → HCID 69838142, compound

HRID 357836Notes

Reaction equation

HRID 357836 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>C1(C)C=CC=CC=1.Cl>[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 3

HCID 7669N-MethylbenzylamineHCID 8857Ethyl AcetateHCID 12424833HCID 12424833, compound

Product 1

HCID 69838142HCID 69838142, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 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 IN 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-5c25c21d33534ba3b18816a50703f24c
Source dataset
uspto-grants-1998_11
Patent number
US05840751

Reaction notes

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