Lithium Hydroxide → 5-[cis-3,5-Dimethyl-1-piperazinyl]-3-pyridinecarboxylic acid

HRID 2234991Notes

Reaction equation

HRID 2234991 reaction equation
[CH3:1][C@H:2]1[NH:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[CH:10]=[C:11]([C:15]([O:17]CC)=[O:16])[CH:12]=[N:13][CH:14]=2)[CH2:3]1.[OH-].[Li+]>O1CCCC1>[CH3:8][C@H:6]1[NH:7][C@@H:2]([CH3:1])[CH2:3][N:4]([C:9]2[CH:10]=[C:11]([C:15]([OH:17])=[O:16])[CH:12]=[N:13][CH:14]=2)[CH2:5]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 58988147Ethyl 5-[cis-3,5-dimethyl-1-piperazinyl]-3-pyridinecarboxylate

Product 1

HCID 589881255-[cis-3,5-Dimethyl-1-piperazinyl]-3-pyridinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 5-[(3R,5S)-3,5-dimethyl-1-piperazinyl]-3-pyridinecarboxylate (D32) (800 mg, 3 mmol) in tetrahydrofuran (5 ml) was treated with 0.5M lithium hydroxide (12 ml, 6 mmol). The mixture was stirred at room temperature for 2 hours. The reaction was quenched with acetic acid (1 ml). The solvent was evaporated and the residue purified on SCX eluting with 2M ammonia in methanol to give the title compound (D33). MS (ES+) m/e 236 [M+H]+.

Workup

  1. customThe reaction was quenched with acetic acid (1 ml)
  2. customThe solvent was evaporated
  3. customthe residue purified on SCX
  4. washeluting with 2M ammonia in methanol

Sources & evidence

ORD record
ord-47e7385d00a8420ea36b40ab580a86e5
Source dataset
uspto-grants-2010_05
Patent number
US07713978B2

Reaction notes

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