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

HRID 1279379Notes

Reaction equation

HRID 1279379 reaction equation
[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

Participants

6

Reactant 2

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

Product 1

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

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 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).

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-adf27a6516f3435aaa4f95c508a66fec
Source dataset
uspto-grants-2002_09
Patent number
US06448270B1

Reaction notes

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