Epichlorohydrin → 1-Methyl-5-(2,3-epoxypropoxy)-8-benzyloxy-3,4-dihydrocarbostyril

HRID 1155571Notes

Reaction equation

HRID 1155571 reaction equation
[CH3:1][N:2]1[C:12]2[C:7](=[C:8]([OH:21])[CH:9]=[CH:10][C:11]=2[O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:6][CH2:5][C:3]1=[O:4].[CH2:22]([CH:24]1[O:26][CH2:25]1)Cl>N1CCCCC1>[CH3:1][N:2]1[C:12]2[C:7](=[C:8]([O:21][CH2:22][CH:24]3[O:26][CH2:25]3)[CH:9]=[CH:10][C:11]=2[O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:6][CH2:5][C:3]1=[O:4]

Participants

4

Reactant 2

HCID 7835EpichlorohydrinHCID 127518361-Methyl-5-hydroxy-8-benzyloxy-3,4-dihydrocarbostyril

Product 1

HCID 127518381-Methyl-5-(2,3-epoxypropoxy)-8-benzyloxy-3,4-dihydrocarbostyrilYield 53.1%

Reagents, catalysts & solvents 1

HCID 8082PiperidineCatalyst

Procedure

5.5 g of 1-methyl-5-hydroxy-8-benzyloxy-3,4-dihydrocarbostyril was added to 15 g of epichlorohydrin, and 12 drops of piperidine were then added thereto followed by stirring at 90° to 100° C. for 3 hours. The unreacted epichlorohydrin and piperidine were evaporated under reduced pressure, and the residue was dissolved in chloroform, washed successively with a 5% aqueous solution of sodium hydroxide and water and dried over anhydrous potassium carbonate. The chloroform was evaporated under reduced pressure, and the residue was purified by silica gel chromatography and then recrystallized from ethanol to afford 3.5 g of 1-methyl-5-(2,3-epoxypropoxy)-8-benzyloxy-3,4-dihydrocarbostyril as yellow needle-like crystals having a melting point of 111°-112.5° C.

Workup

  1. additionwere then added
  2. customThe unreacted epichlorohydrin and piperidine were evaporated under reduced pressure
  3. dissolutionthe residue was dissolved in chloroform
  4. washwashed successively with a 5% aqueous solution of sodium hydroxide and water
  5. dry with materialdried over anhydrous potassium carbonate
  6. customThe chloroform was evaporated under reduced pressure
  7. customthe residue was purified by silica gel chromatography
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-2fc154a80200406ca7afeef94dd9d34a
Source dataset
uspto-grants-1981_11
Patent number
US04302588

Reaction notes

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