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

HRID 723587

반응식

HRID 723587 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 345198Adams' catalyst촉매HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2e561e2e750c4a5b86f2845f87eaf4fa
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07141584B2

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