5-Bromothiophene-2-carbaldehyde → 5-PIPERAZIN-1-YLTHIOPHENE-2-CARBALDEHYDE

HRID 336833Notes

Reaction equation

HRID 336833 reaction equation
Br[C:2]1[S:6][C:5]([CH:7]=[O:8])=[CH:4][CH:3]=1.[N:9]1(C(OC(C)(C)C)=O)[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1>O>[N:9]1([C:2]2[S:6][C:5]([CH:7]=[O:8])=[CH:4][CH:3]=2)[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 784285-Bromothiophene-2-carbaldehydeHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 24631775-PIPERAZIN-1-YLTHIOPHENE-2-CARBALDEHYDEYield 71.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 1.09 g (5.7 mmol) of 5-bromothiophene-2-carboxaldehyde and 3.19 g (17.1 mmol) of tert-butyl piperazine-1-carboxylate in 30 ml of water is heated under reflux for 48 h. The aqueous phase is extracted three times with methylene chloride. The organic phases are combined, dried over sodium sulfate, filtered, and evaporated. The residue is purified by chromatography on silica (MeOH gradient in dichloromethane: 5 to 10%) to yield 0.80 g (70%) of 5-(piperazin-1-yl)thiophene-2-carboxaldehyde in the form of a blue-grey solid.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 48 h
  3. extractionThe aqueous phase is extracted three times with methylene chloride
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is purified by chromatography on silica (MeOH gradient in dichloromethane: 5 to 10%)

Sources & evidence

ORD record
ord-5668f39988284b37ad4c806bd5df46cf
Source dataset
uspto-grants-2014_11
Patent number
US08889711B2

Reaction notes

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