Hydrochloric Acid → HCID 86761160, compound

HRID 505354Notes

Reaction equation

HRID 505354 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[CH2:6][NH:7][CH2:8][CH:9](OC)OC.[CH:19]1[C:24]([CH:25]=O)=[CH:23][C:22]2[O:27][CH2:28][O:29][C:21]=2[CH:20]=1.[ClH:30]>>[ClH:30].[CH3:18][O:17][C:16]1[CH2:15][C:14]2[C:5](=[CH:4][C:3]=1[O:2][CH3:1])[CH:6]=[N:7][C:8]1=[C:9]3[C:19](=[CH:24][C:25]=21)[CH:20]=[C:21]1[O:29][CH2:28][O:27][C:22]1=[CH:23]3

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 8438PiperonalHCID 12378777HCID 12378777, compound

Product 1

HCID 86761160HCID 86761160, compound

Conditions

Temperature
100 °C

Procedure

Concentrated HCl (20 mL) was added to a mixture of amine 12a (2.17 g, 8.51 mmol) and piperonal (10b, 3.0 g, 0.020 mol). The reaction mixture was stirred at 100° C. for 3 h. The reaction mixture was then cooled and washed with ether (50 mL×3). Then it was brought to a basic pH with NH4OH. The mixture was extracted with chloroform (50 mL×4), washed with water (100 mL), dried (Na2SO4) and concentrated. The residue was dissolved in a mixture of organic solvents (50 mL diethyl ether, 100 mL dichloromethane, 100 mL chloroform). The mixture was filtered and HCl (2 M in ether, 40 mL) was added to the filtrate. The yellow precipitate that formed (0.806 g, 26%) was collected by filtration, mp 238-240° C. 1H NMR (300 MHz D2O) δ 8.30 (s, 1H), 6.91 (s, 1H), 6.69 (s, 1H), 6.44 (s, 1H), 6.39 (s, 1H), 5.94 (s, 2H), 3.78 (s, 3H), 3.77 (s, 3H), 3.00 (s, 2H); low resolution ESIMS m/z (rel intensity) 322 (100, M+); IR (KBr) 3429, 3032, 2611, 1623, 1551, 1504, 1489, 1430, 1413, 1379, 1331, 1296, 1273, 1226, 1206, 1172, 1036, 977, 933, 837, 776, 724 cm−1. Anal. Calcd for C19H16NO4Cl(H2O)0.85: C, 61.17; H, 4.78; N, 3.75. Found: C, 61.19; H, 4.77; N, 3.56.

Workup

  1. temperatureThe reaction mixture was then cooled
  2. washwashed with ether (50 mL×3)
  3. extractionThe mixture was extracted with chloroform (50 mL×4)
  4. washwashed with water (100 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in a mixture of organic solvents (50 mL diethyl ether, 100 mL dichloromethane, 100 mL chloroform)
  8. filtrationThe mixture was filtered
  9. additionHCl (2 M in ether, 40 mL) was added to the filtrate
  10. customThe yellow precipitate that formed (0.806 g, 26%)
  11. filtrationwas collected by filtration, mp 238-240° C

Sources & evidence

ORD record
ord-66adce0472b84330afaa41d2321d1088
Source dataset
uspto-grants-2010_08
Patent number
US07781445B2

Reaction notes

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