Diethyl Ether → HCID 15541414, compound

HRID 1861659Notes

Reaction equation

HRID 1861659 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1)(N1C=CN=C1)=[O:2].Cl.[OH:14][CH2:15][CH2:16][NH:17][CH2:18][CH2:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.CCOCC.N1(CCN)C[CH2:35][CH2:34][CH2:33][CH2:32]1>O1CCCC1>[CH:20]1([CH2:19][CH2:18][N:17]([CH2:16][CH2:15][OH:14])[C:1]([NH:8][CH2:12][CH2:11][N:10]2[CH2:9][CH2:35][CH2:34][CH2:33][CH2:32]2)=[O:2])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 33944N-(2-Aminoethyl)piperidineHCID 682631,1'-CarbonyldiimidazoleHCID 22723091HCID 22723091, compound

Product 1

HCID 15541414HCID 15541414, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,1′-Carbonyldiimidazole (740 mg) was dissolved in a solution of 2-(1-piperidyl) ethylamine (0.50 ml) in anhydrous tetrahydrofuran (18 ml) under the nitrogen gas atmosphere and then the mixture was stirred at room temperature for 20 minutes. N-(2-Hydroxyethyl)-2-cyclohexylethylamine hydrochloride (875 mg) was added to the reaction solution and the mixture was refluxed with heating for 3 hours. Ether was added to the reaction solution with ice cooling, the resulting mixture was washed with saturated aqueous sodium hydrogen carbonate solution and saturated sodium chloride aqueous solution in this order, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting oily product was purified through the silica gel column chromatography to give the title compound (Compound 1-1, 1.01 g).

Workup

  1. temperaturethe mixture was refluxed
  2. temperaturewith heating for 3 hours
  3. washthe resulting mixture was washed with saturated aqueous sodium hydrogen carbonate solution and saturated sodium chloride aqueous solution in this order
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting oily product was purified through the silica gel column chromatography

Sources & evidence

ORD record
ord-2e81b3f91f58496393295e8fcf187196
Source dataset
uspto-grants-2003_03
Patent number
US06534499B2

Reaction notes

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