4-Iodoaniline → 4-(4-(4-Benzylpiperidin-1-yl)but-1-ynyl)aniline

HRID 1279375노트

반응식

HRID 1279375 반응식
[CH2:1]([N:5]1[CH2:10][CH2:9][CH:8]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7][CH2:6]1)[CH2:2][C:3]#[CH:4].I[C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=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>[NH2:23][C:22]1[CH:24]=[CH:25][C:19]([C:4]#[C:3][CH2:2][CH2:1][N:5]2[CH2:6][CH2:7][CH:8]([CH2:11][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:9][CH2:10]2)=[CH:20][CH:21]=1

참가 물질

6

반응물 2

HCID 108934-IodoanilineHCID 106093551-(3-Butynyl)-4-benzylpiperidine

생성물 1

HCID 107107074-(4-(4-Benzylpiperidin-1-yl)but-1-ynyl)aniline수율 16%

시약·촉매·용매 3

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

실험 절차

A mixture of 1-(but-3-yn-1-yl)-4-benzylpiperidine (227 mg, 1.00 mmol), 4-iodoaniline (263 mg, 1.20 mmol), copper (I) iodide (15 mg), PdCl2(PPh3)2 (28 mg) 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 pale yellow oil (50 mg, 16%): 1H NMR (CDCl3) 1.29 (m, 2 H) , 1.51 (m, 1 H), 1.66 (m, 2 H), 1.99 (m, 2 H), 2.58 (m, 6 H), 2.91 (m, 2 H), 3.73 (m, 2 H), 6.55 (d, J=7.8 Hz, 2 H), 7.13-7.28 (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-65fd516456af44779f898fdab938fa3f
출처 데이터셋
uspto-grants-2002_09
특허 번호
US06448270B1

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