Formaldehyde → HCID 44608178, compound

HRID 388203Notes

Reaction equation

HRID 388203 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.[CH3:24][N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1>CO>[CH3:24][N:25]1[CH2:30][CH2:29][N:28]([CH2:22][C:5]2[C:6]([OH:20])=[C:7]3[C:8](=[C:3]([O:2][CH3:1])[C:4]=2[OH:21])[O:9][C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:11][C:12]3=[O:13])[CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 531671-MethylpiperazineHCID 5281703Wogonin

Product 1

HCID 44608178HCID 44608178, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
51 °C

Procedure

The mixture of Wogonin (28.4 g), methanol (350 ml), 37% formaldehyde solution (8.04 ml), 4-N-methyl-piperazine (10.1 g) was stirred under for 4 hours at 51° C., then precipitates were removed by filtration and washed several times with methanol, after drying under reduced pressure at 55° C. to get the product as orange red solid 38.6 g of purity 99.7%. m.p.: 179° C. MS: (API-ES) m/z 397.5 [M+H]+, 419.5 [M+Na]+, 1H NMR (DMSO-d6/CF3COOD, 400 MHz): δ 8.12˜8.14 (m, 2H, Ar-2′,6′-H), 7.64˜7.66 (m, 3H, Ar-3′,4′,5′-H), 7.15 (s, 1H, 3-H), 4.44 (s, 2H, CH2), 3.96 (s, 3H, 8-OCH3), 3.43-3.74 (m, 8H, CH2), 2.93 (s, 3H, N—CH3).

Workup

  1. customprecipitates
  2. customwere removed by filtration
  3. washwashed several times with methanol
  4. customafter drying under reduced pressure at 55° C.

Sources & evidence

ORD record
ord-1576da26277c4a4188b83028139ddebe
Source dataset
uspto-grants-2013_02
Patent number
US08377895B2

Reaction notes

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