Lithium Hydroxide → 2-Amino-5-(4-methyl-piperazin-1-ylmethyl)benzoic acid

HRID 591814Notes

Reaction equation

HRID 591814 reaction equation
C[O:2][C:3](=[O:19])[C:4]1[CH:9]=[C:8]([CH2:10][N:11]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]2)[CH:7]=[CH:6][C:5]=1[NH2:18].[OH-].[Li+]>O.CO>[NH2:18][C:5]1[CH:6]=[CH:7][C:8]([CH2:10][N:11]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]2)=[CH:9][C:4]=1[C:3]([OH:19])=[O:2]

Participants

5

Reactant 2

HCID 3939Lithium Hydroxide2×HCID 666710482-Amino-5-(4-methyl-piperazin-1-ylmethyl)benzoic acid methyl ester

Product 1

HCID 666711232-Amino-5-(4-methyl-piperazin-1-ylmethyl)benzoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 2-amino-5-(4-methyl-piperazin-1-ylmethyl)benzoic acid methyl ester (4.30 g, 10.0 mmol) in water (30 mL) and methanol (10 mL) was added lithium hydroxide (1.26 g, 30.0 mmol); the mixture was stirred at room temperature for 12 hours. An additional amount of lithium hydroxide (0.6 g, 15.0 mmol) was added, and heated at 40° C. for 15 hours; TLC indicated completion of the reaction. The mixture was cooled, concentrated, the residue was adjusted to pH ˜5 with 6 N HCl, and evaporated to dryness, to provide crude 2-amino-5-(4-methyl-piperazin-1-ylmethyl)benzoic acid. Yield: 6.2 g, along with inorganic salt. It was used in the next step without further purification.

Workup

  1. temperatureheated at 40° C. for 15 hours
  2. customcompletion of the reaction
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-ff471476d4144877ac00ce466dee6cde
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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