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

HRID 1279375Notes

Reaction equation

HRID 1279375 reaction equation
[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

Participants

6

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-65fd516456af44779f898fdab938fa3f
Source dataset
uspto-grants-2002_09
Patent number
US06448270B1

Reaction notes

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