Triethylamine → HCID 22348107, compound

HRID 897238Notes

Reaction equation

HRID 897238 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][C:13]([F:16])([F:15])[F:14])[CH:10]=2)[O:5][C:4](=[O:17])[CH:3]=1.[O:18]1[C:22]2[CH:23]=[CH:24][C:25]([CH2:27][N:28]3[CH2:33][CH2:32][CH:31]([NH2:34])[CH2:30][CH2:29]3)=[CH:26][C:21]=2[O:20][CH2:19]1.C(N(CC)CC)C>CN1CCCC1=O.O>[O:18]1[C:22]2[CH:23]=[CH:24][C:25]([CH2:27][N:28]3[CH2:33][CH2:32][CH:31]([NH:34][C:2]4[C:11]5[C:6](=[CH:7][CH:8]=[C:9]([O:12][C:13]([F:16])([F:15])[F:14])[CH:10]=5)[O:5][C:4](=[O:17])[CH:3]=4)[CH2:30][CH2:29]3)=[CH:26][C:21]=2[O:20][CH2:19]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 116731041-[(2H-1,3-Benzodioxol-5-yl)methyl]piperidin-4-amineHCID 223481574-Chloro-6-(trifluoromethoxy)-2H-1-benzopyran-2-one

Product 1

HCID 22348107HCID 22348107, compoundYield 52.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
220 °C

Procedure

To a suspension of 4-chloro-6-trifluoromethoxycoumarin (0.04 g, 0.15 mmol) in 1 ml N-methylpyrrolidone in a Smith reaction vial was added 1-benzo[1,3]dioxol-5-ylmethyl-piperidin-4-ylamine (0.039 g, 0.16 mmol) followed by 0.042 ml of triethylamine. The reaction vessel was sealed with a crimper and the reaction heated at 220° C. for 20 minutes in a Smith Synthesizer. The reaction was diluted with 20 ml water and extracted with 3×10 ml ethyl acetate. The combined organic layers were dried over MgSO4, filtered, evaporated and chromatographed using 2% CH3OH:DCM to afford 36.4 mg (52%) of a white solid. MS (ESI (+)) m/e 463 (M+H)+; 1H NMR (300 MHz, MeOD4) δ ppm 1.65-1.75 (m, 2H), 2.0-2.1 (m, 2H), 2.25 (m, 2H), 3.0 (m, 2H), 3.5 (s, 2H), 3.6 (m, 1H), 5.37 (s, 1H), 5.9 (s, 2H), 6.75 (m, 2H), 6.9 (m, 1H), 7.45 (m, 1H), 7.55 (m, 1H), 8.10 (br s, 1H).

Workup

  1. customin a Smith reaction
  2. customThe reaction vessel was sealed with a crimper
  3. extractionextracted with 3×10 ml ethyl acetate
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customchromatographed

Sources & evidence

ORD record
ord-6691484d0ffd42bfb54b387faa5d4678
Source dataset
uspto-grants-2005_07
Patent number
US06921821B2

Reaction notes

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