Formaldehyde → HCID 44608498, compound

HRID 388211Notes

Reaction equation

HRID 388211 reaction equation
[CH3:1][O:2][C:3]1[C:4]([OH:21])=[CH:5][C:6]([OH:20])=[C:7]2[C:12](=[O:13])[CH:11]=[C:10]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[O:9][C:8]=12.[CH2:22]=O.[NH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1>CO>[OH:20][C:6]1[C:5]([CH2:22][N:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)=[C:4]([OH:21])[C:3]([O:2][CH3:1])=[C:8]2[C:7]=1[C:12](=[O:13])[CH:11]=[C:10]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[O:9]2

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8082PiperidineHCID 5281703Wogonin

Product 1

HCID 44608498HCID 44608498, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

The mixture of Wogonin (28.4 g), methanol (350 ml), 37% formaldehyde solution (8.1 ml), piperidine (8.5 g) was stirred under for 4.5 hours at 55° C., then precipitates were removed by filtration and washed several times with methanol, after drying under reduced pressure at 65° C. to get the product as yellow solid 35.3 g of purity 99.2%. MS: (API-ES) m/z 382.5[M+H]+, 404.5[M+Na]+; 1H NMR (DMSO-d6, 400 MHz) δ 8.05˜8.06 (m, 2H, Ar-2′,6′-H), 7.60˜7.61 (m, 3H, Ar-3′,4′,5′-H), 6.89 (s, 1H, 3-H), 3.95 (s, 2H, CH2), 3.83 (s, 3H, 8-OCH3), 2.79 (s, 4H, CH2), 1.64 (m, 4H, CH2), 1.50 (m, 2H, CH2).

Workup

  1. customprecipitates
  2. customwere removed by filtration
  3. washwashed several times with methanol
  4. customafter drying under reduced pressure at 65° C.

Sources & evidence

ORD record
ord-2f29206025414c6196951b5d1fd0245d
Source dataset
uspto-grants-2013_02
Patent number
US08377895B2

Reaction notes

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