Water → HCID 49785059, compound

HRID 2061073Notes

Reaction equation

HRID 2061073 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]([F:14])([F:13])[CH2:9][CH2:8]1.C(O[Cl:23])(C)(C)C.O>CO>[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]([F:14])([F:13])[CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 962WaterHCID 521297Tert-Butyl hypochloriteHCID 67310805HCID 67310805, compound

Product 1

HCID 49785059HCID 49785059, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1-(3-Amino-3-methylbutyl)-4,4-difluoro-1-methylpiperidinium chloride hydrochloride (0.57 g, 1.94 mmol) in methanol (15 mL) was cooled in an ice bath for 15 min. t-BuOCl (0.69 mL, 3 equiv, 5.82 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., and 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 white solid, (0.52 g, 83.1%). 1H NMR (D2O, 400 MHz): δ 1.47 (s, 6H), 2.27-2.32 (m, 2H), 2.422-2.56 (m, 4H), 3.10 (s, 3H), 3.55-3.61 (m, 2H), 3.65-3.69 (m, 4H). LRMS (ESI+) for C11H21Cl2F2N2+ (289.1); Found: 289 (M+).

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 white solid, (0.52 g, 83.1%)

Sources & evidence

ORD record
ord-f8e449e8fb614a8e8f23d1c3977e99b2
Source dataset
uspto-grants-2012_10
Patent number
US08278482B2

Reaction notes

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