Formaldehyde → HCID 44608331, compound

HRID 388205Notes

Reaction equation

HRID 388205 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][CH:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1>CO>[OH:20][C:6]1[C:5]([CH2:22][N:28]2[CH2:29][CH2:30][CH:25]([OH:24])[CH2:26][CH2:27]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 79341Piperidin-4-olHCID 5281703Wogonin

Product 1

HCID 44608331HCID 44608331, 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-hydroxy-piperidine (10.2 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 orange red solid 38.5 g of purity 99.4%. MS: (API-ES) m/z 398.5 [M+H]+420.5 [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), 6.90 (s, 1H, 3-H), 3.94 (s, 2H, CH2), 3.83 (s, 3H, 8-OCH3), 3.65-3.67 (m, 1H, CH), 2.62, 2.98 (m, 4H, CH2), 1.51, 1.83 (m, 4H, 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-393bfda58eca478196d1a0d83a8eabd8
Source dataset
uspto-grants-2013_02
Patent number
US08377895B2

Reaction notes

Loading…