Lithium Hydroxide → HCID 44253223, compound

HRID 2036049Notes

Reaction equation

HRID 2036049 reaction equation
C([O:3][C:4]([C:6]1[O:7][C:8]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:20][CH2:19][N:18]([CH2:21][C:22]4[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:23]=4[Cl:29])[CH2:17][CH2:16]3)=[C:11]([CH3:30])[C:9]=2[CH:10]=1)=[O:5])C.[OH-].[Li+]>C1COCC1.O.CO>[Cl:28][C:27]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:29])[C:22]=1[CH2:21][N:18]1[CH2:17][CH2:16][N:15]([C:12]2[CH:13]=[CH:14][C:8]3[O:7][C:6]([C:4]([OH:5])=[O:3])=[CH:10][C:9]=3[C:11]=2[CH3:30])[CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67201414HCID 67201414, compound

Product 1

HCID 44253223HCID 44253223, compoundYield 166.9%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of 5-[4-(2,6-Dichloro benzyl)-piperazine-1-yl]-4-methyl-benzofuran-2-carboxylic acid ethyl ester (0.08 g, 0.0001 mol) in THF:Water:Methanol (3:2:1) mixture (19 ml) was added lithium hydroxide (0.02 g, 0.0005 mol) at 0° C. The reaction mixture was stirred for 2 hours. The completion of the reaction was confirmed by TLC. Solvent was concentrated under reduced pressure added ice water. The pH of the mixture was made acidic with 1N HCl and the solid separated was filtered. After drying under vacuum, isolated 5-[4-(2,6-Dichloro benzyl)-piperazine-1-yl]-4-methyl-benzofuran-2-carboxylic acid (70 mg, 94%).

Workup

  1. concentrationSolvent was concentrated under reduced pressure
  2. additionadded ice water
  3. customthe solid separated
  4. filtrationwas filtered
  5. customAfter drying under vacuum

Sources & evidence

ORD record
ord-6e10d3334f2e4e6281cc568e03b01456
Source dataset
uspto-grants-2013_11
Patent number
US08575161B2

Reaction notes

Loading…