Tert-Butyl hypochlorite → HCID 86642705, compound

HRID 2061083Notes

Reaction equation

HRID 2061083 reaction equation
[ClH:1].[Cl-:2].[NH2:3][C:4]([CH3:17])([CH3:16])[CH2:5][CH2:6][N+:7]1([CH3:15])[CH2:12][CH2:11][C:10]([CH3:14])([CH3:13])[CH2:9][CH2:8]1.C(O[Cl:23])(C)(C)C>CO.O>[Cl-:23].[Cl:1][N:3]([Cl:2])[C:4]([CH3:17])([CH3:16])[CH2:5][CH2:6][N+:7]1([CH3:15])[CH2:12][CH2:11][C:10]([CH3:13])([CH3:14])[CH2:9][CH2:8]1

Participants

5

Reactant 2

HCID 521297Tert-Butyl hypochloriteHCID 67319342HCID 67319342, compound

Product 1

HCID 86642705HCID 86642705, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 1-(3-amino-3-methylbutyl)-1,4,4-trimethylpiperidinium chloride hydrochloride (0.50 g, 1.73 mmol) in a mixture of methanol (10 mL) and water (8 mL) was cooled in an ice bath for 15 min. t-BuOCl (0.62 mL, 3 equiv, 5.21 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 concentrated under reduced pressure to yield a colorless oil. This oil was dissolved into water and purified via reverse phase chromatography on a Shimadzu Prep-LC utilizing water/acetonitrile and 0.05% acetic acid as modifier. Fractions were collected monitoring UV absorbance at 215 nm. Fractions were pooled and concentrated via rotovap with the water bath set at 25° C. to give a pale yellow foam, (0.373 g, 67.8%). 1H NMR (D2O, 400 MHz): δ 1.06 (s, 3H), 1.07 (s, 3H), 1.46 (s, 6H), 1.64-1.80 (m, 4H), 2.21-2.27 (m, 2H), 3.05 (s, 3 H), 3.35-3.45 (m, 6H). LRMS (ESI+) for C13H27Cl2N2+ (281.1); Found: 281, 283 (M+, M2H+).

Workup

  1. additionwas added in one portion via syringe to the colorless solution
  2. customto give a deep yellow solution
  3. concentrationconcentrated under reduced pressure
  4. customto yield a colorless oil
  5. custompurified via reverse phase chromatography on a Shimadzu Prep-LC
  6. customFractions were collected
  7. concentrationconcentrated via rotovap with the water bath
  8. customset at 25° C.
  9. customto give a pale yellow foam, (0.373 g, 67.8%)

Sources & evidence

ORD record
ord-c33c38dd0b40443390d85d76ffcd27bc
Source dataset
uspto-grants-2012_10
Patent number
US08278482B2

Reaction notes

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