Piperidine → HCID 58124916, compound

HRID 1971700Notes

Reaction equation

HRID 1971700 reaction equation
[CH3:1][N:2]([C:10]([CH3:16])([CH2:12][CH2:13][C:14]#[CH:15])[CH3:11])[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].N1CCCCC1.I[C:24]1[S:25][CH:26]=[CH:27][CH:28]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C.[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>[CH3:1][N:2]([C:10]([CH3:16])([CH2:12][CH2:13][C:14]#[C:15][C:24]1[S:25][CH:26]=[CH:27][CH:28]=1)[CH3:11])[C:3](=[O:9])[O:4][C:5]([CH3:7])([CH3:8])[CH3:6]

Participants

8

Reactant 3

HCID 8082PiperidineHCID 189212-IodothiopheneHCID 58124849HCID 58124849, compound

Product 1

HCID 58124916HCID 58124916, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 130 mg of 12f, 100 μl of piperidine, 75 μl of 2-iodothiophene, 10 mg of CuI and 14 mg of PdCl2(PPh3)2 in 2 ml of degassed toluene was stirred under N2 for 3 hr. The reaction mixture was diluted with 20 ml of ethyl acetate and washed with water, dried and concentrated. The crude material was purified by chromatography over a silica column, using a gradient of pentane/diethyl ether as eluent. This provided 130 mg of 12g as colorless oil; Rf 0.60 (heptane/ether 3/1).

Workup

  1. washwashed with water
  2. customdried
  3. concentrationconcentrated
  4. customThe crude material was purified by chromatography over a silica column

Sources & evidence

ORD record
ord-2d25f7a8a1854aea99f9992f47317a73
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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