Benzylamine → N-benzyl-2-(1,3-dioxolan-2-yl)ethanamine
Reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.Br[CH2:19][CH2:20][CH:21]1[O:25][CH2:24][CH2:23][O:22]1>C(#N)C.C(OCC)(=O)C>[CH2:1]([NH:8][CH2:19][CH2:20][CH:21]1[O:25][CH2:24][CH2:23][O:22]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
6
Procedure
To a mixture of benzylamine (2.18 mL, 20.0 mmol) and di-iso-propylethylamine (2.61 mL, 15.0 mmol) in acetonitrile (30 mL) was added 2-(2-bromoethyl)-1,3-dioxolane (1.17 mL, 10.0 mmol). The reaction mixture was stirred at room temperature for 72 hours. The reaction mixture was diluted with ethyl acetate and washed with water and brine. The organic phase was dried (magnesium sulfate), filtered and the solvent evaporated at reduced pressure. The residue was purified by flash column chromatography eluting with 0 to 4% methanol/dichloromethane to afford the title compound (0.836 g, 40%).
Workup
- washwashed with water and brine
- dry with materialThe organic phase was dried (magnesium sulfate)
- filtrationfiltered
- customthe solvent evaporated at reduced pressure
- customThe residue was purified by flash column chromatography
- washeluting with 0 to 4% methanol/dichloromethane
Sources & evidence
- ORD record
- ord-a0285b814ca049f996ac3f2e4bd4e2b1
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08980913B2
Reaction notes
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