Piperonal → HCID 10051310, compound

HRID 897241Notes

Reaction equation

HRID 897241 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([Cl:20])[CH:5]=[C:6]2[C:11]=1[O:10][C:9](=[O:12])[CH:8]=[C:7]2[NH:13][CH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.[CH:21]1[C:26]([CH:27]=O)=[CH:25][C:24]2[O:29][CH2:30][O:31][C:23]=2[CH:22]=1.C([O-])([O-])=O.[K+].[K+]>>[Br:1][C:2]1[CH:3]=[C:4]([Cl:20])[CH:5]=[C:6]2[C:11]=1[O:10][C:9](=[O:12])[CH:8]=[C:7]2[NH:13][CH:14]1[CH2:15][CH2:16][N:17]([CH2:27][C:26]2[CH:21]=[CH:22][C:23]3[O:31][CH2:30][O:29][C:24]=3[CH:25]=2)[CH2:18][CH2:19]1

Participants

4

Reactant 3

HCID 8438PiperonalHCID 11430Potassium CarbonateHCID 22348119HCID 22348119, compound

Product 1

HCID 10051310HCID 10051310, compound

Procedure

8-bromo-6-chloro-4-(piperidin-4-ylamino)-chromen-2-one and piperonal were allowed to react under reductive alkylation conditions for 44 hours at room temperature, then treated with 1 M K2CO3, extracted with CH2Cl2, filtered through silica gel (5 g SepPak), rinsed with 95:5 CH2Cl2:MeOH, and concentrated. Purification by silica gel preparatory plate (0.25 mm×20 cm×20 cm) developed with 95:5 CH2Cl2:MeOH to give the title compound as a white solid (6 mg). 1H NMR (300 MHz, ppm, DMSO-d6) δ 1.6 (m, 2H), 1.9 (m, 2H), 2.1 (m, 2H), 2.8 (m, 2H), 3.4-3.5 (m, 3H), 5.33 (s, 1H), 5.99 (s, 2H), 6.77 (m, 1H), 6.85 (m, 2H), 7.38 (m, 1H), 8.05 (d, J=2 Hz, 1H), 8.36 (d, J=2 Hz, 1H). MS(ESI) 493 (M+H), 491 (M−H).

Workup

  1. customto react under reductive alkylation conditions for 44 hours at room temperature
  2. extractionextracted with CH2Cl2
  3. filtrationfiltered through silica gel (5 g SepPak)
  4. washrinsed with 95:5 CH2Cl2
  5. concentrationMeOH, and concentrated
  6. customPurification by silica gel preparatory plate (0.25 mm×20 cm×20 cm)

Sources & evidence

ORD record
ord-6a2b357565144607a09166d0c19459cc
Source dataset
uspto-grants-2005_07
Patent number
US06921821B2

Reaction notes

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