Dimethylamine → tert-Butyl 4-[1-dimethylamino-3-(6-methylpyridin-2-yl)prop-2-ynyl]piperidine-1-carboxylate

HRID 1895964Notes

Reaction equation

HRID 1895964 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[N:4]=1)#[CH:2].[C:10]([N:17]1[CH2:22][CH2:21][CH:20]([CH:23]=O)[CH2:19][CH2:18]1)([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].[CH3:25][NH:26][CH3:27]>O.[Cu]I>[CH3:25][N:26]([CH3:27])[CH:23]([CH:20]1[CH2:21][CH2:22][N:17]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:18][CH2:19]1)[C:2]#[C:1][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[N:4]=1

Participants

6

Reactant 3

HCID 674DimethylamineHCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylateHCID 134006352-Ethynyl-6-methylpyridine

Product 1

HCID 68724984tert-Butyl 4-[1-dimethylamino-3-(6-methylpyridin-2-yl)prop-2-ynyl]piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolvent

Procedure

A mixture of 2-ethynyl-6-methyl-pyridine (0.08 g, 0.7 mmol), 1-Boc-4-piperidinecarboxaldehyde (0.1 g, 0.47 mmol), CuI (0.001 g, 0.11 mmol) and 33% w/w aqueous dimethylamine (0.077 mL, 0.56 mmol) in water (3 mL) was sonicated for 2 h in a laboratory ultrasonic bath. Afterwards, it was extracted with EtOAc and the combined organic layers were washed with brine, dried on Na2SO4 and evaporated to dryness in vacuo to give a crude, which was purified by automated flash liquid chromatography (Horizon™-Biotage) eluting with EtOAc—Petroleum Ether 1:1 affording the title product (0.11 g).

Workup

  1. customwas sonicated for 2 h in a laboratory ultrasonic bath
  2. extractionAfterwards, it was extracted with EtOAc
  3. washthe combined organic layers were washed with brine
  4. customdried on Na2SO4
  5. customevaporated to dryness in vacuo
  6. customto give a crude, which
  7. customwas purified by automated flash liquid chromatography (Horizon™-Biotage)
  8. washeluting with EtOAc—Petroleum Ether 1:1 affording the title product (0.11 g)

Sources & evidence

ORD record
ord-60d77b5b2c8e4b16bca1bfff2f5673b3
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

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