Sodium Iodide → HCID 19772580, compound

HRID 344684Notes

Reaction equation

HRID 344684 reaction equation
[CH3:1][O:2][C:3]([C:5]1([N:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:12](=[O:15])[CH2:13][CH3:14])[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)=[O:4].Br[CH2:23][CH2:24][OH:25].C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>C(#N)C>[OH:25][CH2:24][CH2:23][N:8]1[CH2:9][CH2:10][C:5]([C:3]([O:2][CH3:1])=[O:4])([N:11]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:12](=[O:15])[CH2:13][CH3:14])[CH2:6][CH2:7]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 108982-BromoethanolHCID 2724431Methyl 4-[phenyl(propanoyl)amino]piperidine-4-carboxylate

Product 1

HCID 19772580HCID 19772580, compoundYield 96.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-methoxycarbonyl-4-(N'-phenylpropionamido)piperidine (7.34 g, 25 mmol), 2-bromoethanol (3.96 g, 32 mmol), sodium carbonate (20.0 g, 189 mmol), and sodium iodide (1.0 g) in acetonitrile (200ml) was heated to reflux for three days. The reaction mixture was cooled and filtered. The filtrate was concentrated under vacuum yielding an oily residue. The residue was chromatographed on silica gel (250 g; ethyl acetate/hexane; 1:4) to yield 1-(2-hydroxyethyl)-4-methoxycarbonyl-4-(N'-phenylpropionamido)piperidine (8.1 g, 96%) as an oil.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for three days
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under vacuum
  6. customyielding an oily residue
  7. customThe residue was chromatographed on silica gel (250 g; ethyl acetate/hexane; 1:4)

Sources & evidence

ORD record
ord-0a1d0857030e4e41999a13bd5ef55443
Source dataset
uspto-grants-1991_10
Patent number
US05053411

Reaction notes

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