Tert-Butyl hypochlorite → HCID 56966369, compound

HRID 1770707Notes

Reaction equation

HRID 1770707 reaction equation
[Cl-:1].[NH2:2][C:3]([CH3:14])([CH3:13])[CH2:4][CH2:5][N+:6]([CH2:9][CH2:10][O:11][CH3:12])([CH3:8])[CH3:7].C(O[Cl:20])(C)(C)C>CO>[Cl-:20].[Cl:1][N:2]([Cl:20])[C:3]([CH3:14])([CH3:13])[CH2:4][CH2:5][N+:6]([CH2:9][CH2:10][O:11][CH3:12])([CH3:7])[CH3:8]

Participants

4

Reactant 2

HCID 521297Tert-Butyl hypochloriteHCID 86665522HCID 86665522, compound

Product 1

HCID 56966369HCID 56966369, compoundYield 168.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 3-amino-N-(2-methoxyethyl)-N,N,3-trimethylbutan-1-aminium chloride (830 mg, 3.5 mmol) in methanol (14 ml) was cooled to 0° C. tert-Butylhypochlorite (984 μl, 2.5 mmol) was added. The resulting solution was stirred for 45 minutes at 0° C. and then concentrated under reduced pressure. The residue was purified by reverse phase high pressure liquid chromatography eluting from a C18 column with a gradient of 5 to 95% CH3CN in water (with 0.01% acetic acid) to give 618 mg of a clear oil. 1H NMR (D2O, 400 MHz) δ 1.33 (s, 6H), 2.15-2.20 (m, 2H), 3.08 (s, 6H), 3.40 (s, 3H), 3.40-3.44 (m, 2H), 3.49-3.51 (m, 2H), 3.80-3.82 (m, 2H). 13C NMR (D2O, 100 MHz) δ 73.1, 65.5, 62.9, 62.9, 62.8, 60.8, 60.8, 60.7, 58.2, 51.5, 51.4, 51.4, 31.3, 22.8; LRMS (ESI/APCI) m/z 257 [M]+.

Workup

  1. additionwas added
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by reverse phase high pressure liquid chromatography
  4. washeluting from a C18 column with a gradient of 5 to 95% CH3CN in water (with 0.01% acetic acid)

Sources & evidence

ORD record
ord-cedaceb8c0884844ae9aa7173f48129e
Source dataset
uspto-grants-2016_02
Patent number
US09248117B2

Reaction notes

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