Potassium Carbonate → 1-(3-Butynyl)-4-(4-chlorophenyl)-4-hydroxypiperidine

HRID 324533노트

반응식

HRID 324533 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:14])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:4]([N:11]1[CH2:10][CH2:9][C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)([OH:14])[CH2:13][CH2:12]1)[CH2:3][C:2]#[CH:7]

참가 물질

4

반응물 2

HCID 11430Potassium CarbonateHCID 382824-(4-Chlorophenyl)-4-hydroxypiperidine

생성물 1

HCID 222257381-(3-Butynyl)-4-(4-chlorophenyl)-4-hydroxypiperidine수율 145.3%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixutre of 3-butyn-1-methanesulfate (1.48 g, 0.01 mol), 4-(p-chlorophenyl)-4-hydroxypiperidine (2.54 g, 0.012 mol) and potassium carbonate (4.14 g, 0.03 mol) in 25 mL of acetonitrile was refluxed for 12 hrs. The mixture was filtered and washed with ethyl acetate (3×30 mL). The filtrate was evaporated in vacuo and was purified by flash chromatography to give 2.30 g (87%) of the product as a white solid. mp 98-100° C. 1H NMR (CHCl3) 1.550 (s, 1 H), 1.749 (m, 2 H), 1.997 (m, 1 H), 2.109 (m, 2 H), 2.423 (m, 4 H), 2.655 (m, 2 H), 2.798 (m, 2 H), 7.329 (d, J=7.2 Hz, 2 H), 7.429 (d, J=7.2 Hz, 2 H).

후처리

  1. filtrationThe mixture was filtered
  2. washwashed with ethyl acetate (3×30 mL)
  3. customThe filtrate was evaporated in vacuo
  4. customwas purified by flash chromatography

출처 및 근거

ORD 기록
ord-a20d98fdbc614b749c5cf7f644d6bc42
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06218404B1

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