Formaldehyde → HCID 44608175, compound

HRID 388200Notes

Reaction equation

HRID 388200 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]([C:7]2[O:20][C:12]3=[CH:13][C:14]([OH:19])=[C:15]([OH:18])[C:16]([OH:17])=[C:11]3[C:9](=[O:10])[CH:8]=2)=[CH:5][CH:6]=1.[CH2:21]=O.[OH:23][CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1>CO>[OH:17][C:16]1[C:15]([OH:18])=[C:14]([OH:19])[C:13]([CH2:21][N:29]2[CH2:30][CH2:31][N:26]([CH2:25][CH2:24][OH:23])[CH2:27][CH2:28]2)=[C:12]2[C:11]=1[C:9](=[O:10])[CH:8]=[C:7]([C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1)[O:20]2

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 76771-(2-Hydroxyethyl)piperazineHCID 5281605Baicalein

Product 1

HCID 44608175HCID 44608175, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
51 °C

Procedure

The mixture of Baicalein (27 g), methanol (350 ml), 37% formaldehyde solution (8.04 ml), 4-N-hydroxyethyl-piperazine (13.1 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 yellow solid 40.3 g of purity 98.5%. m.p.: 192° C. MS: (API-ES) m/z 413.3 [M+H]+, 435.2 [M+Na]+, 825.5[2M+H]+, 847.5[2M+Na]+; 1H NMR (DMSO-d6/CFCOOD, 400 MHz): δ 8.18˜8.19 (m, 2H, Ar-2′,6′-H), 7.61˜7.67 (m, 3H, Ar-3′,4′,5′-H), 7.09 (s, 1H, 3-H), 4.73 (s, 2H, CH2), 3.76 (t, 2H, —CH2—OH), 3.59-3.69 (m, 8H, CH2), 3.33 (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 55° C.

Sources & evidence

ORD record
ord-fb295a112b1442128f8363f07572d934
Source dataset
uspto-grants-2013_02
Patent number
US08377895B2

Reaction notes

Loading…