Triethylamine hydrochloride → HCID 70805217, compound

HRID 1519028Notes

Reaction equation

HRID 1519028 reaction equation
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12]O[C:10]=1[CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:17][CH:18]([F:21])[CH2:19][NH2:20].Cl.C(N(CC)CC)C>N1C=CC=CC=1>[CH2:1]([O:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12][N:20]([CH2:19][CH:18]([F:21])[F:17])[C:10]=1[CH3:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11130Triethylamine hydrochlorideHCID 1362742,2-DifluoroethanamineHCID 14901193-Benzyloxy-2-methyl-4-pyrone

Product 1

HCID 70805217HCID 70805217, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
110 °C

Procedure

3-(Benzyloxy)-2-methyl-4H-pyran-4-one (432 mg, 2.0 mmol) was mixed with 2,2-difluoroethylamine (655 mg, 8.0 mmol) and triethylamine hydrochloride (1.10 g, 8.0 mmol) in pyridine (6 mL) in a sealed vial. The reaction mixture was heated at 110° C. for overnight. The solid was filtered and washed with ethyl acetate. The filtrate was concentrated under reduced pressure and the residue was mixed with water, and then extracted with ethyl acetate. The organic layer was washed with water and brine. The product was purified by column chromatography on silica gel with 5% methanol in ethyl acetate as eluant to give 3-(benzyloxy)-1-(2,2-difluoroethyl)-2-methylpyridin-4(1H)-one (337 mg) as pale-yellow solid. Yield=60%; 1H NMR (MeOD-D4, 90 MHz) δ (ppm): 7.66 (d, J=7.1 Hz, 1H), 7.16-7.55 (m, 5H), 6.46 (d, J=7.1 Hz, 1H), 5.55 (t, J=55.0 Hz, 1H), 4.45 (t, J=14.8 Hz, 1H) and 2.20 (s, 3H); MS m/z 280 [M+1]+.

Workup

  1. filtrationThe solid was filtered
  2. washwashed with ethyl acetate
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. additionthe residue was mixed with water
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with water and brine
  7. customThe product was purified by column chromatography on silica gel with 5% methanol in ethyl acetate as eluant

Sources & evidence

ORD record
ord-bd8f160910444c8fb924e165a294f4d2
Source dataset
uspto-grants-2015_07
Patent number
US09073865B2

Reaction notes

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