Tert-Butyl hypochlorite → HCID 46198502, compound
Reaction equation
[Cl-:1].[NH2:2][C:3]([CH3:14])([CH3:13])[CH2:4][CH2:5][N+:6]1([CH3:12])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.C(O[Cl:20])(C)(C)C>CO.O>[Cl-:20].[Cl:1][N:2]([Cl:20])[C:3]([CH3:14])([CH3:13])[CH2:4][CH2:5][N+:6]1([CH3:12])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
A solution of 1-(3-amino-3-methylbutyl)-1-methylpiperidinium chloride (1.00 g, 3.80 mmol) in a mixture of methanol (6 mL) and water (6 mL) was cooled in an ice bath for 15 min. t-BuOCl (1.3 mL, 3.0 equiv, 11.4 mmol) was added in one portion via syringe to the colorless solution to give a deep yellow solution. The reaction mixture was stirred for 30 min at 0° C. Then the methanol was removed under reduced pressure and the crude solid was purified via reverse phase chromatography on a Shimadzu Prep-LC utilizing water/methanol and 0.05% acetic acid as modifier. Fractions were collected monitoring UV absorbance at 215 nm. Fractions were pooled and concentrated under reduced pressure at 25° C. to give a white solid, (0.92 g, 83%). 1H NMR (D2O, 400 MHz): δ 1.46 (s, 6H), 1.52-1.55 (m, 2H), 1.70-1.95 (m, 4H), 2.20-2.28 (m, 2H), 3.05 (s, 3H), 3.35-3.48 (m, 6H). LRMS (ESI+) for C11H23Cl2N2+ (253.1); Found: 253, 255 (M+, M2H+).
Workup
- additionwas added in one portion via syringe to the colorless solution
- customto give a deep yellow solution
- customThen the methanol was removed under reduced pressure
- customthe crude solid was purified via reverse phase chromatography on a Shimadzu Prep-LC
- customFractions were collected
- concentrationconcentrated under reduced pressure at 25° C.
- customto give a white solid, (0.92 g, 83%)
Sources & evidence
- ORD record
- ord-e2af223d38e14b55850ffdc9d95ba551
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08278482B2
Reaction notes
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