Ethylene Glycol → HCID 67428715, compound

HRID 659084Notes

Reaction equation

HRID 659084 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].[CH2:5]([N:12]1[CH2:17][CH2:16][CH:15]([N:18]([CH:25]([CH3:27])[CH3:26])[C:19](=[O:24])[CH2:20][CH2:21][CH2:22]Cl)[CH2:14][CH2:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClCCl>[CH2:5]([N:12]1[CH2:13][CH2:14][CH:15]([N:18]([CH:25]([CH3:26])[CH3:27])[C:19](=[O:24])[CH2:20][CH2:21][CH2:22][O:3][CH2:2][CH2:1][OH:4])[CH2:16][CH2:17]1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 67427949HCID 67427949, compound

Product 1

HCID 67428715HCID 67428715, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of ethylene glycol (15 mL, 268 mmol) and N-(1-benzylpiperidin-4-yl)-N-isopropyl 4-chlorobutyramide (5.0 g, 14.9 mmol) was heated at 140° C. for 2 h in the presence of a catalytic amount p-toluenesulfonic acid. The reaction mixture was then dissolved in dichloromethane and the solution washed with 1 N sodium hydroxide, aqueous sodium bicarbonate solution and brine; and dried over MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography (dichloromethane/methanol/ammonium hydroxide: 90/9/1) to give 2.72 g of the title intermediate as viscous oil (51% yield).

Workup

  1. washthe solution washed with 1 N sodium hydroxide, aqueous sodium bicarbonate solution and brine
  2. dry with materialand dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash column chromatography (dichloromethane/methanol/ammonium hydroxide: 90/9/1)

Sources & evidence

ORD record
ord-54840c867c0142a08c0a5fdd80123444
Source dataset
uspto-grants-2011_12
Patent number
US08080565B2

Reaction notes

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