1-Bromododecane → 4-Dodecyl-5-methyl-3-morpholinone
Reaction equation
[H-].[Na+].[CH3:3][CH:4]1[NH:9][C:8](=[O:10])[CH2:7][O:6][CH2:5]1.[CH2:11](Br)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>C1(C)C=CC=CC=1>[CH2:22]([N:9]1[CH:4]([CH3:3])[CH2:5][O:6][CH2:7][C:8]1=[O:10])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH3:11]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 3.00 g of 60% sodium hydride and 100 ml of benzene was incorporated dropwise with a solution of 3.00 g of L-2-amino-1-propanol in 10 ml of benzene, thereafter agitated at room temperature for a whole day, freed from the solvent by distillation off at reduced pressure to obtain a residue which was dissolved in ethyl acetate and subjected to column chromatography thereby to obtain 3.25 g of 5-methyl-3-morpholinone. A mixture of 1.24 g of 60% sodium hydride and 100 ml of toluene was incorporated dropwise with a solution of 3.25 g of 5-methyl-3-morpholinone in 10 ml of toluene, refluxed for one hour, incorporated with 7.05 g of lauryl bromide, further refluxed for a whole day, filtered to remove insoluble materials. The filtrate obtained was washed, dried and freed from the solvent by distillaton off at reduced pressure, subjected to column chromatography and finally distilled to obtain 5.69 g of colorless 4-(n-dodecyl)-5-methyl-3-morpholinone having the following appearance, column temperature and analysis:
Workup
- temperaturefurther refluxed for a whole day
- filtrationfiltered
- customto remove insoluble materials
- customThe filtrate obtained
- washwas washed
- customdried
- distillationfinally distilled
Sources & evidence
- ORD record
- ord-6d1d4a44f05840ed8db06ef7fa88f1d5
- Source dataset
- uspto-grants-1989_11
- Patent number
- US04882359
Reaction notes
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