Epichlorohydrin → HCID 21450252, compound

HRID 596667Notes

Reaction equation

HRID 596667 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([CH2:8][CH2:9][C:10]([NH:12][CH3:13])=[O:11])=[O:7])=[CH:4][CH:3]=1.[CH2:16]([CH:18]1[O:20][CH2:19]1)Cl.N1CCCCC1.[OH-].[Na+]>ClCCl>[O:20]1[CH2:19][CH:18]1[CH2:16][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([CH2:8][CH2:9][C:10]([NH:12][CH3:13])=[O:11])=[O:7])=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 7835EpichlorohydrinHCID 8082PiperidineHCID 14798Sodium HydroxideHCID 21450220HCID 21450220, compound

Product 1

HCID 21450252HCID 21450252, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of finely ground 3-(4-hydroxybenzoyl)-N-methylpropionamide (20.7 g, 0.1 mole), epichlorohydrin (77 g, 0.83 mole), and piperidine (0.5 ml) was heated on a steam bath for 90 minutes. Evaporation under reduced pressure gave a viscous oil which was dissolved in dichloromethane (500 ml) and shaken with dilute sodium hydroxide (100 ml). The organic phase was washed with water, dried and evaporated to a slurry. Addition of ether gave the required 3-[4-(2,3-epoxypropoxy)benzoyl]-N-methylpropionamide (21.36g.,81%) which was recrystallised from chloroform/ether, m.p. 133°-140° C.

Workup

  1. temperaturewas heated on a steam bath for 90 minutes
  2. customEvaporation under reduced pressure
  3. customgave a viscous oil which
  4. washThe organic phase was washed with water
  5. customdried
  6. customevaporated to a slurry
  7. additionAddition of ether

Sources & evidence

ORD record
ord-0ca1b70f6b664cb1bd1203c2612d1269
Source dataset
uspto-grants-1977_03
Patent number
US04011321

Reaction notes

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