Methanol → HCID 20148593, compound

HRID 569011Notes

Reaction equation

HRID 569011 reaction equation
Cl[CH2:2][CH2:3][NH:4][C:5](=[O:8])[CH2:6][CH3:7].[OH:9][CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.C(=O)([O-])[O-].[Na+].[Na+].CO>C(#N)C>[OH:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:2][CH2:3][NH:4][C:5](=[O:8])[CH2:6][CH3:7])[CH2:12][CH2:11]1

Participants

6

Reactant 4

HCID 887MethanolHCID 10340Sodium CarbonateHCID 79341Piperidin-4-ol2×HCID 12709128HCID 12709128, compound

Product 1

HCID 20148593HCID 20148593, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of N-(2-chloroethyl)propanamide (27.1 g, 0.20 mol), 4-hydroxypiperidine (20.2 g, 0.20 mol) and anhydrous sodium carbonate (10.6 g, 0.10 mol) in acetonitrile (120 ml) was stirred at reflux under nitrogen for 20 hours. Additional 4-hydroxypiperidine (20.2 g, 0.20 mol) was added and the mixture stirred at reflux for 3 days. After concentrating under reduced pressure, the residue was dissolved in ethyl acetate and a minimum amount of water. The aqueous layer was saturated with sodium chloride and re-extracted several times with ethyl acetate. The organic extracts were combined, dried (Na2SO4), filtered and concentrated to give 13.1 g of crude product. Pure product was obtained by flash chromatography over silica gel and elution with 20% methanol-80% chloroform.

Workup

  1. temperatureat reflux under nitrogen for 20 hours
  2. stirringthe mixture stirred
  3. temperatureat reflux for 3 days
  4. concentrationAfter concentrating under reduced pressure
  5. dissolutionthe residue was dissolved in ethyl acetate
  6. extractionre-extracted several times with ethyl acetate
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give 13.1 g of crude product

Sources & evidence

ORD record
ord-2be570458a9b475ca58195d704726c5d
Source dataset
uspto-grants-1988_03
Patent number
US04731369

Reaction notes

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