1-Chloroethyl chloroformate → HCID 70085604, compound

HRID 376833Notes

Reaction equation

HRID 376833 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5](/[CH:7]=[C:8]2\[CH2:9][N:10](C)[CH2:11][CH2:12][CH2:13]\2)[O:4][N:3]=1.[Cl:15]C(OC(Cl)=O)C>C1(C)C=CC=CC=1>[ClH:15].[CH3:1][C:2]1[CH:6]=[C:5](/[CH:7]=[C:8]2\[CH2:9][NH:10][CH2:11][CH2:12][CH2:13]\2)[O:4][N:3]=1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 10583909HCID 10583909, compound

Product 1

HCID 70085604HCID 70085604, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of (Z)-3-(3-methyl-5-isoxazolyl)methylene-1-methylpiperidine (1.3 g, 6.5 mmol) in toluene (50 ml) was added 1-chloroethylchloroformate (1.3 g, 10 mmol). The reaction mixture was heated at reflux for 5 h. The reaction mixture was evaporated and methanol (50 ml) was added. The reaction mixture was heated at reflux for 1 h and evaporated. The crude compound was purified by column chromatography (eluent: methylene chloride/methanol/ammonium hydroxide (25%): 8/2/0.5). The free base was crystallized as the hydrochloride from ethyl acetate giving the title compound in 350 mg yield. M.p. 232-235° C. (Compound 5).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 5 h
  3. customThe reaction mixture was evaporated
  4. additionmethanol (50 ml) was added
  5. temperatureThe reaction mixture was heated
  6. temperatureat reflux for 1 h
  7. customevaporated
  8. customThe crude compound was purified by column chromatography (eluent: methylene chloride/methanol/ammonium hydroxide (25%): 8/2/0.5)
  9. customThe free base was crystallized as the hydrochloride from ethyl acetate giving the title compound in 350 mg
  10. customyield

Sources & evidence

ORD record
ord-023f1803027a4a44bdb365436f1fdbbc
Source dataset
uspto-grants-2000_02
Patent number
US06022868

Reaction notes

Loading…