Methyl Acrylate → HCID 20225023, compound

HRID 1249179Notes

Reaction equation

HRID 1249179 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH:13]([NH2:17])[CH2:14][CH2:15][CH3:16])[CH2:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[C:18]([O:22][CH3:23])(=[O:21])[CH:19]=[CH2:20]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH:13]([NH:17][CH2:20][CH2:19][C:18]([O:22][CH3:23])=[O:21])[CH2:14][CH2:15][CH3:16])[CH2:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 7294Methyl Acrylate2×HCID 13083217HCID 13083217, compound

Product 1

HCID 20225023HCID 20225023, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1-[1-(3,4-dichlorophenyl)cyclobutyl]butylamine (2 g), methyl acrylate (2 g) and toluene (10 ml) was heated under reflux with stirring for a total of 20 hours. Methyl acrylate (0.5 ml) was added, and heating under reflux and stirring were continued for 3 days. The solvent was removed in vacuo, and the oily residue as purified by chromatography on a silica column using a mixture of 9 parts petroleum ether (b.p. 40°-60°) and 1 part acetone as eluant. From the eluate methyl 3-{1-[1-(3,4-dichlorophenyl)cyclobutyl]butylamino}propanoate was obtained as a pale yellow oil, the physical properties of which were not determined.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. temperatureheating
  4. temperatureunder reflux
  5. stirringstirring
  6. waitwere continued for 3 days
  7. customThe solvent was removed in vacuo
  8. customthe oily residue as purified by chromatography on a silica column
  9. additiona mixture of 9 parts petroleum ether (b.p. 40°-60°) and 1 part acetone as eluant

Sources & evidence

ORD record
ord-1ccfe852267a41ed8a4c3a0ebd56ab3f
Source dataset
uspto-grants-1986_12
Patent number
US04629727

Reaction notes

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