Hydrochloric Acid → 4-[(Piperidin-4-yl)methyl]aniline

HRID 634832

反応式

HRID 634832 の反応式
[N+:1]([C:4]1[CH:16]=[CH:15][C:7]([CH2:8][C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)=[CH:6][CH:5]=1)([O-])=O.Cl.O>C(O)C.[Pt](=O)=O>[NH:12]1[CH2:13][CH2:14][CH:9]([CH2:8][C:7]2[CH:6]=[CH:5][C:4]([NH2:1])=[CH:16][CH:15]=2)[CH2:10][CH2:11]1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 141294-(4-Nitrobenzyl)pyridine

生成物 1

HCID 109978244-[(Piperidin-4-yl)methyl]aniline収率 86.3%

試薬・触媒・溶媒 2

HCID 345198Adams' catalyst触媒HCID 702Ethanol溶媒

実験手順

A mixture of 4-(4-nitrobenzyl)pyridine (12.85 g, 60 mmol), platinum(IV) oxide (1.0 g), 12N hydrochloric acid (5 ml, 60 mmol), water (5 ml) in ethanol (200 ml) was hydrogenated at 40 psi in a Parr apparatus for 12 hours. The reaction mixture was concentrated in vacuo, and the residue was diluted with cold water and basified with 10% sodium hydroxide solution. The resulting mixture was extracted into ethyl acetate. The combined organic extracts were washed with water and brine, dried (Na2SO4), and concentrated in vacuo. The residue on crystallization from ethyl acetate/hexanes gave 4-(piperidin-4-ylmethyl)-phenylamine (9.85 g, 86%) as a white crystalline solid, m.p. 110-113° C.

後処理

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionthe residue was diluted with cold water and basified with 10% sodium hydroxide solution
  3. extractionThe resulting mixture was extracted into ethyl acetate
  4. washThe combined organic extracts were washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue on crystallization from ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-1c56253fd1cd4e318801626525f419b7
出典データセット
uspto-grants-2001_02
特許番号
US06184242B2

関連ノート

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