Methanol → HCID 44578088, compound

HRID 388199Notes

Reaction equation

HRID 388199 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.[CH3:21][N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.[CH3:28]O>>[OH:17][C:16]1[C:15]([OH:18])=[C:14]([OH:19])[C:13]([CH2:21][N:22]2[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]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

4

Reactant 3

HCID 887MethanolHCID 531671-MethylpiperazineHCID 5281605Baicalein

Product 1

HCID 44578088HCID 44578088, compound

Conditions

Temperature
55 °C

Procedure

The mixture of Baicalein (100 g), methanol 2 L, 37% formaldehyde solution (36.5 ml), 4-N-methyl-piperazin solution (45 g) was stirred under for 4 hours at 55° 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 113 g of purity 99.9%. m.p.: 280˜282° C. UV: λmax(alcohol) 278, 330 nm; MS: (API-ES) m/z 383.1 [M+H]+, 405.1 [M+Na]+; IR: 3400, 3050, 2925, 2861, 1637, 1570, 1509 cm−1; 1H NMR (DMSO-d6, 400 MHz): δ 2.14 (s, 3H, CH3), 2.62 (s, 8H, N—CH2), 3.44 (s, 7-OH), 3.96 (s, 2H, 8-CH2), 6.87 (s, 1H, 3-H), 7.46˜7.54 (m, 3H, Ar—H), 8.01˜8.02 (m, 2H, Ar—H), 8.11 (s, 6-OH), 12.64 (s, 1H, 5-OH).

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-9dfb7b2ac695420484687e1bc1295a15
Source dataset
uspto-grants-2013_02
Patent number
US08377895B2

Reaction notes

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