Formaldehyde → HCID 44608179, compound

HRID 388204Notes

Reaction equation

HRID 388204 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.[OH:24][CH2:25][CH2:26][N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1>CO>[OH:24][CH2:25][CH2:26][N:27]1[CH2:32][CH2:31][N:30]([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])[CH2:29][CH2:28]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 76771-(2-Hydroxyethyl)piperazineHCID 5281703Wogonin

Product 1

HCID 44608179HCID 44608179, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

The mixture of Wogonin (28.4 g), methanol (350 ml), 37% formaldehyde solution (8.04 ml), 4-N-hydroxyethyl-piperazine (13.1 g) was stirred under for 4 hours at 50° 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 41.7 g of purity 99.5%. MS: (API-ES) m/z 427.5[M+H]+, 449.5[M+Na]+; 1H NMR (DMSO-d6/CF3COOD, 400 MHz): δ 8.11˜8.13 (m, 2H, Ar-2′,6′-H), 7.62˜7.67 (m, 3H, Ar-3′,4′,5′-H), 7.11 (s, 1H, 3-H), 4.45 (s, 2H, CH2), 3.98 (s, 3H, 8-OCH3), 3.78 (t, 2H, —CH2—OH), 3.49-3.69 (m, 8H, CH2), 3.36 (t, 2H, N—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-3a30d0dc51d64006baa6b2b0f973180c
Source dataset
uspto-grants-2013_02
Patent number
US08377895B2

Reaction notes

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