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4-Iodoaniline → 1-[4-(4-Amino-phenyl)-but-3-ynyl]-4-benzyl-piperidin-4-ol

HRID 1279379
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인쇄 미리보기

반응식

HRID 1279379 반응식
[CH2:1]([C:8]1([OH:18])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]#[CH:17])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I[C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1>CCN(CC)CC.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:24][C:23]1[CH:25]=[CH:26][C:20]([C:17]#[C:16][CH2:15][CH2:14][N:11]2[CH2:12][CH2:13][C:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)([OH:18])[CH2:9][CH2:10]2)=[CH:21][CH:22]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 2

HCID 108934-IodoanilineHCID 106817044-Benzyl-1-(3-butynyl)-4-hydroxypiperidine

생성물 1

HCID 106167371-[4-(4-Amino-phenyl)-but-3-ynyl]-4-benzyl-piperidin-4-ol수율 30%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물
촉매
HCID 8471Triethylamine용매

실험 절차

A mixture of 4-benzyl-1-(but-3-yn-1-yl)-4-hydroxypiperidine (243 mg, 1.00 mmol), 4-iodoaniline (219 mg, 1.00 mmol), copper(I) iodide (40 mg), PdCl2(PPh3)2 (50 mg, 0.04 mmol) in 10 mL of Et3N is stirred at room temperature under N2 for 20 hr. The mixture is filtered and washed with Et3N (3×15 mL). The filtrate is evaporated in vacuo and is purified by flash chromatography to give the product as a brown oil (100 mg, 30%): 1H NMR (CDCl3) 1.49 (m, 3 H), 1.72 (m, 2 H), 2.38 (m, 2 H), 2.55-2.66 (m, 6 H), 2.74 (s, 2 H), 3.75 (s, 2 H), 6.52 (d, J=8.4 Hz, 2 H), 7.15-7.30 (m, 7 H).

후처리

  1. filtrationThe mixture is filtered
  2. washwashed with Et3N (3×15 mL)
  3. customThe filtrate is evaporated in vacuo
  4. customis purified by flash chromatography

출처 및 근거

ORD 기록
ord-adf27a6516f3435aaa4f95c508a66fec
출처 데이터셋
uspto-grants-2002_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06448270B1

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