Water → 5-Phenyl-1,3-dihydro-2H-azepin-2-one
Reaction equation
C([O:5][C:6]1[CH2:12][CH:11]=[C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:9]=[CH:8][N:7]=1)CCC.O>C(O)C>[C:13]1([C:10]2[CH:9]=[CH:8][NH:7][C:6](=[O:5])[CH2:12][CH:11]=2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 150 °C
Procedure
The 2-butoxy-5-phenyl-3H-azepine (908 g, 3.42 moles) is dissolved in 2B-3 ethanol (8172 mL) and de-ionized water (2724 mL). The solution is charged to an autoclave and heated to 150° C. for 20 hours. The solution is cooled to room temperature and concentrated under reduced pressure. Residual water is removed by azeotropic distillation from toluene (2×2 L). The residual solids are dissolved in toluene (1.7 L) and heated between 95 to 100° C. The solution is cooled to <90° C. and heptane (about 4.8 mL/g) is added. The solution is allowed to cool to room temperature, and then cooled to 0 to 5° C. using an ice bath. The solids are filtered, washed with heptane, and dried to give the title compound (559 g, 88%) as a light brown solid.
Workup
- additionThe solution is charged to an autoclave
- temperatureThe solution is cooled to room temperature
- concentrationconcentrated under reduced pressure
- customResidual water is removed by azeotropic distillation from toluene (2×2 L)
- dissolutionThe residual solids are dissolved in toluene (1.7 L)
- temperatureheated between 95 to 100° C
- temperatureThe solution is cooled to <90° C.
- additionheptane (about 4.8 mL/g) is added
- temperatureto cool to room temperature
- temperaturecooled to 0 to 5° C.
- filtrationThe solids are filtered
- washwashed with heptane
- customdried
Sources & evidence
- ORD record
- ord-326bbf8ce60143d98bd0cdf568298848
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08188069B2
Reaction notes
Loading…