Water → Ethyl 2-benzoylaminocyclohexene-1-carboxylate

HRID 592113Notes

Reaction equation

HRID 592113 reaction equation
[NH2:1][C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].N1C=CC=CC=1.[CH2:19](Cl)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[OH2:27]>C(#N)C>[C:19]([NH:1][C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9])(=[O:27])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7503Benzyl ChlorideHCID 312929Ethyl 2-aminocyclohex-1-ene-1-carboxylate

Product 1

HCID 12221540Ethyl 2-benzoylaminocyclohexene-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
40 °C

Procedure

In a 2000 ml flask were charged ethyl 2-aminocyclohexene-1-carboxylate (80.0 g, 472.8 mmol), pyridine (37.4 g, 472.8 mmol), and acetonitrile (190 ml), and the mixture was dissolved by heating to 40° C. While keeping the mixture at 40-50° C., a solution (126 ml) of benzyl chloride (63.14 g, 449.2 mmol) in acetonitrile was added dropwise. The mixture was stirred at 50-60° C. for 1.5 hr, cooled, and water (631 ml) was added dropwise at 20-30° C. over 30 min. After stirring at the same temperature for 30 min, the precipitate was collected by filtration and washed with water (631 ml). The obtained powder was dried under reduced pressure at 60° C. yield 119.62 g, 97%.

Workup

  1. dissolutionthe mixture was dissolved
  2. customat 40-50° C.
  3. temperaturecooled
  4. stirringAfter stirring at the same temperature for 30 min
  5. filtrationthe precipitate was collected by filtration
  6. washwashed with water (631 ml)
  7. customThe obtained powder was dried under reduced pressure at 60° C. yield 119.62 g, 97%

Sources & evidence

ORD record
ord-94ed0bdd34b242e4be3b874d738373b2
Source dataset
uspto-grants-2016_01
Patent number
US09238667B2

Reaction notes

Loading…