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

HRID 723587

反応式

HRID 723587 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-2e561e2e750c4a5b86f2845f87eaf4fa
出典データセット
uspto-grants-2006_11
特許番号
US07141584B2

関連ノート

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