Vanillic Acid → HCID 71239650, compound

HRID 1403204Notes

Reaction equation

HRID 1403204 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[OH:30][C:31]1[CH:39]=[CH:38][C:34]([C:35]([OH:37])=O)=[CH:33][C:32]=1[O:40][CH3:41]>C(Cl)Cl>[OH:30][C:31]1[CH:39]=[CH:38][C:34]([C:35]([N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)=[O:37])=[CH:33][C:32]=1[O:40][CH3:41]

Participants

6

Reactant 4

HCID 8468Vanillic AcidHCID 531671-MethylpiperazineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 71239650HCID 71239650, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Methylpiperazine (0.58 mL, 5.2 mmol), HOBt (0.70 g, 5.2 mmol.) and EDCl (1.0 g, 5.2 mmol) were added to a solution of 4-hydroxy-3-methoxybenzoic acid (0.69 g, 4.0 mmol.) in dry DCM (40 mL). The mixture was stirred at room temperature for 16 h, washed with saturated aqueous sodium bicarbonate (20 mL), brine, dried over sodium sulphate and evaporated to give the title compound (0.96 g, 96%).

Workup

  1. washwashed with saturated aqueous sodium bicarbonate (20 mL), brine
  2. dry with materialdried over sodium sulphate
  3. customevaporated

Sources & evidence

ORD record
ord-d68c9c33cab04ecfb8a80352d6942e0e
Source dataset
uspto-grants-2014_12
Patent number
US08912200B2

Reaction notes

Loading…