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

HRID 336833ノート

反応式

HRID 336833 の反応式
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

参加物

4

反応物 2

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

生成物 1

HCID 24631775-PIPERAZIN-1-YLTHIOPHENE-2-CARBALDEHYDE収率 71.5%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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%)

出典と根拠

ORDレコード
ord-5668f39988284b37ad4c806bd5df46cf
出典データセット
uspto-grants-2014_11
特許番号
US08889711B2

反応ノート

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