Formaldehyde → HCID 44608176, compound

HRID 388201Notes

Reaction equation

HRID 388201 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][CH:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1>CO>[OH:17][C:16]1[C:15]([OH:18])=[C:14]([OH:19])[C:13]([CH2:21][N:27]2[CH2:28][CH2:29][CH:24]([OH:23])[CH2:25][CH2:26]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 79341Piperidin-4-olHCID 5281605Baicalein

Product 1

HCID 44608176HCID 44608176, 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-hydroxy-piperidine (10.2 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 37.02 g of purity 99.2%. m.p.: 221° C. MS: (API-ES) m/z 384.2[M+H]+, 767.5[2M+H]+, 789.5 [2M+Na]+; 1H NMR (DMSO-d6, 400 MHz): δ 8.05˜8.07 (m, 2H, Ar-2′,6′-H), 7.58˜7.59 (m, 3H, Ar-3′,4′,5′-H), 6.87 (s, 1H, 3-H), 4.17 (s, 2H, CH2), 3.67 (m, 1H, CH), 2.68, 3.03 (m, 2H, CH2), 2.71, 3.05 (m, 2H, CH2), 1.52, 1.82 (m, 2H, CH2), 1.53, 1.84 (m, 2H, 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-ab3c3312c5974630954fa7df12f601d6
Source dataset
uspto-grants-2013_02
Patent number
US08377895B2

Reaction notes

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