Ethanol → 1-(2-Methoxyethyl)piperidine-4-carbaldehyde

HRID 1795158ノート

反応式

HRID 1795158 の反応式
COC1C=C(N)C=C[C:8]=1[O:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16]O[CH2:14][CH2:13]1.[CH2:19]([OH:21])[CH3:20]>[Pd]>[CH3:8][O:9][CH2:10][CH2:11][N:12]1[CH2:13][CH2:14][CH:20]([CH:19]=[O:21])[CH2:16][CH2:17]1

参加物

4

反応物 2

HCID 702EthanolHCID 22185405HCID 22185405、化合物

生成物 1

HCID 178939541-(2-Methoxyethyl)piperidine-4-carbaldehyde

試薬・触媒・溶媒 1

HCID 23938Palladium触媒

実験手順

4-[2-(2-Methoxy-4-nitro-phenoxy)-ethyl]-morpholine To a solution of (1-(2-hydroxyethyl)-morpholine) (1.94 ml, 16 mmol) in dimethylformamide was added sodium hydride [60% dispersion in oil] (544 mg, 16 mmol). After stirring at room temperature for 10 min, a solution of (1-chloro-2-methoxy-4-nitro-benzene) (3 g, 16 mmol) in dimethylformamide (10 ml) was added dropwise. The reaction mixture was left stirring at room temperature for 16 hours, concentrated, then the residue dissolved in ethyl acetate and washed with water. The organic phase was dried with magnesium sulphate, concentrated and the residue purified by column chromatography on silica gel to afford the title compound; MS(ES+) m/e 283 [M+H]+. Step 2. 3-Methoxy-4-(2-morpholin-4-yl-ethoxy)-phenylamine To a solution of the product of Step 1 (2.3 g, 8.6 mmol) in ethanol (100 ml) was added 10% palladium on charcoal (50 mg). The mixture was then stirred at room temperature under an atmosphere of hydrogen for 16 hours, filtered through celite and concentrated to give the title compound; MS(ES+) m/e 252 [M+H]+.

後処理

  1. filtrationfiltered through celite and
  2. concentrationconcentrated

出典と根拠

ORDレコード
ord-c1f4e202548643b8a6af7552c715765a
出典データセット
uspto-grants-2006_04
特許番号
US07026336B1

反応ノート

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