Lithium Hydroxide → 2-(Piperazin-1-yl)thiazole-5-carboxaldehyde

HRID 1058364Notes

Reaction equation

HRID 1058364 reaction equation
Cl[C:2]1[S:3][C:4]([CH:7]=[O:8])=[CH:5][N:6]=1.[NH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.[OH-].[Li+]>O1CCCC1>[N:9]1([C:2]2[S:3][C:4]([CH:7]=[O:8])=[CH:5][N:6]=2)[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 4837PiperazineHCID 14797652-Chloro-1,3-thiazole-5-carbaldehyde

Product 1

HCID 186730122-(Piperazin-1-yl)thiazole-5-carboxaldehydeYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-chlorothiazole-5-carboxaldehyde (Example 53; 378 mg, 2.6 mmol) in aqueous tetrahydrofuran (9.75 mL tetrahydrofuran, 0.25 mL of water, 40:1) at 25° C. was added piperazine (0.55 g, 6.4 mmol) followed by lithium hydroxide (129 mg, 3.0 mmol). After stirring for 24 h at room temperature, the solvents were removed under reduced pressure. The residual solid was diluted with water (50 mL) and neutralized to pH 7 with 1N hydrochloric acid solution. The resulting solids were filtered, washed with water, dried under vacuum and flash chromatographed (silica gel, 10% methanol in dichloromethane) to yield 2-(piperazin-1-yl)thiazole-5-carboxaldehyde (191 mg, 38% yield) as a yellow solid.

Workup

  1. customthe solvents were removed under reduced pressure
  2. additionThe residual solid was diluted with water (50 mL)
  3. filtrationThe resulting solids were filtered
  4. washwashed with water
  5. customdried under vacuum and flash
  6. customchromatographed (silica gel, 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-1e2adf16d479442c9f8e0a1c6e9b68b1
Source dataset
uspto-grants-2003_02
Patent number
US06515124B2

Reaction notes

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