Piperidine → HCID 71533690, compound

HRID 531417Notes

Reaction equation

HRID 531417 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([N:10]([CH:14]([CH3:16])[CH3:15])[CH2:11][C:12]#[CH:13])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[S:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[N:19]=[C:18]1[CH2:26][C:27](OCC)=[O:28].N1CCCCC1>C(O)C>[S:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[N:19]=[C:18]1[C:26]1[C:27](=[O:28])[O:1][C:2]2[C:3]([CH:4]=1)=[CH:6][CH:7]=[C:8]([N:10]([CH:14]([CH3:16])[CH3:15])[CH2:11][C:12]#[CH:13])[CH:9]=2

Participants

5

Reactant 3

HCID 8082PiperidineHCID 359796Ethyl (1,3-benzothiazol-2-yl)acetateHCID 89494760HCID 89494760, compound

Product 1

HCID 71533690HCID 71533690, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution in which the 2-hydroxy-4-(isopropyl(prop-2-ynyl)amino)benzaldehyde (1.8 g, 8.28 mmol) compound of Chemical Formula 4 was dissolved in ethanol (15 mL), ethyl 2-(benzo[d]thiazol-2-yl)acetate (1.83 g, 8.28 mmol) and piperidine (1.63 mL, 16.56 mmol) were added consecutively at room temperature. The reaction mixture was heated under reflux for 2 hours, cooled to room temperature, and 3-(benzo[d]thiazol-2-yl)-7-(isopropyl(prop-2-ynyl)amino)-2H-chromen-2-one (1.54 g, 50%) was obtained by filtering the precipitated solid. 1H NMR (500 MHz, CDCl3) d 8.94 (s, 1H), 8.02 (d, 1H, J=8.2 Hz), 7.94 (d, 1H, J=7.8 Hz), 7.54 (d, 1H, J=8.7 Hz), 7.47-7.50 (m, 1H), 7.35-7.38 (m, 1H), 6.88 (dd, 1H, J=2.3, 8.7 Hz), 6.80 (d, 1H, J=2.3 Hz), 4.21-4.26 (m, 1H), 4.04 (d, 2H, J=2.3 Hz), 2.26 (t, 1H, J=2.2 Hz), 1.34 (d, 6H, J=6.4 Hz); 13C NMR (125 MHz, CDCl3) d 161.5, 161.0, 156.7, 152.6, 152.4, 142.0, 136.4, 130.6, 126.2, 124.7, 122.3, 121.7, 113.9, 111.0, 109.8, 98.8, 80.0, 72.3, 49.5, 33.5, 20.2 (2).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 2 hours

Sources & evidence

ORD record
ord-089dac8c3dc14488bb3628e3e837d1d4
Source dataset
uspto-grants-2016_05
Patent number
US09354234B2

Reaction notes

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