Triethylamine → HCID 21842639, compound

HRID 1737453Notes

Reaction equation

HRID 1737453 reaction equation
[C:1]1([CH:7]2[CH2:13][C:12](=[O:14])[O:11][C:9](=[O:10])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.CN.[CH2:18]([N:20](CC)CC)C>C1COCC1>[CH3:18][NH:20][C:9]([CH2:8][CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:13][C:12]([OH:11])=[O:14])=[O:10]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 2978824-Phenyloxane-2,6-dioneHCID 6364545Methylamine hydrochloride2×

Product 1

HCID 21842639HCID 21842639, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-phenylglutaric anhydride (500 mg, 2.63 mmol) in THF was added to a mixture of methylamine hydrochloride (266 mg, 3.94 mmol) and triethylamine (1.1 mL, 0.80 g, 7.9 mmol) in 4.0 mL of THEF. After 1.5 h, additional methylamine hydrochloride (177 mg, 2.62 mmol) and triethylamine (0.36 mL, 0.26 g, 2.6 mmol) were added and stirring was continued overnight at room temperature. The reaction was partitioned between 50 mL of ethyl acetate and 25 mL of 2.0 N aqueous HCl. The aqueous layer was extracted with 2×25 mL of ethyl acetate. The combined ethyl acetate layers were washed with 50 mL of brine, dried over sodium sulfate, and evaporated to give 518 mg of the title compound as a white solid. 1NMR (400 MHz, CD3OD): δ 7.29-7.22 (m, 4H), 7.20-7.14 (m, 1H), 3.58 (tt, 1H, J=9, 7 Hz), 2.68 (dd, 1H, J=15, 7 Hz), 2.59 (dd, 1H, J=15, 9 Hz), 2.57 (s, 3H), 2.55 (dd, 1H, J=15, 7 Hz), 2.44 (dd, 1H, J=15, 9 Hz). Mass spectrum (NH3 /CI): m/z=222 (M+1).

Workup

  1. waitwas continued overnight at room temperature
  2. customThe reaction was partitioned between 50 mL of ethyl acetate and 25 mL of 2.0 N aqueous HCl
  3. extractionThe aqueous layer was extracted with 2×25 mL of ethyl acetate
  4. washThe combined ethyl acetate layers were washed with 50 mL of brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-7744ece2469e487e8b78ad2c906445db
Source dataset
uspto-grants-1999_10
Patent number
US05962462

Reaction notes

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