Sulfuric Acid → 4-Benzyl-2-(chloromethyl)morpholine
Reaction equation
ClC1C=CC=C2C=1CCN2[C:11]([O:19][CH2:20][CH2:21][NH:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([CH2:17][Cl:18])[CH:12](CC=O)O.S(=O)(=O)(O)O.[OH-].[Na+]>O>[CH2:23]([N:22]1[CH2:21][CH2:20][O:19][CH:11]([CH2:17][Cl:18])[CH2:12]1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 150 °C
Procedure
41.25 g of 2-[2-(4-chloro-2,3-dihydroindol-1-yl)-2-oxoethyl-2-(2-benzylaminoethoxy)-3-chloropropan-1-ol previously obtained are placed in a 250 ml round-bottomed flask equipped with a condenser, and then 50 ml of concentrated sulfuric acid (d=1.84) are added dropwise. The temperature increases, and the water formed condenses in the condenser. The reaction medium is then heated for one hour at 150° C., then cooled to ambient temperature (20° C.), before being poured slowly onto ice; the reaction medium is brought to pH=10 with 40% NaOH, and then extracted with toluene (2×150 ml), and the organic phases are combined, dried over magnesium sulfate, filtered and evaporated under reduced pressure. 4-Benzyl-2-chloromethylmorpholine is isolated (20.30 g, light brown oil, yield=54%) and is used in the next step.
Workup
- customare placed in a 250 ml round-bottomed flask
- customequipped with a condenser
- temperatureThe temperature increases
- temperaturecooled to ambient temperature (20° C.)
- additionbefore being poured slowly onto ice
- extractionextracted with toluene (2×150 ml)
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- customevaporated under reduced pressure
Sources & evidence
- ORD record
- ord-b5926b1b6fac45fd9cbdad262a5bd910
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09133168B2
Reaction notes
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