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36421-15-5

36421-15-5 Structure

36421-15-5 Structure
IdentificationBack Directory
[Name]

N-(3-chloropropyl)dibutylamine
[CAS]

36421-15-5
[Synonyms]

NSC51133
N-(3-ChL
Einecs 253-027-7
Dronedarone Intermediate 2
Dibutyl(3-chloropropyl)aMine
1-Dibutylamino-3-chloropropane
N-(3-chloropropyl)dibutylamine
1-Chloro-3-di-N-butylaminopropane
Dronedarone Hydrochloride IMpurity F
N-(3-Chloropropyl) dibutyl amine (NCA)
N-butyl-N-(3-chloropropyl)butan-1-aMine
1-Butanamine,N-butyl-N-(3-chloropropyl)-
N-(3-Chloropropyl)dibutylamine CAS 36421-15-5
[EINECS(EC#)]

253-027-7
[Molecular Formula]

C11H24ClN
[MDL Number]

MFCD13185966
[MOL File]

36421-15-5.mol
[Molecular Weight]

205.77
Chemical PropertiesBack Directory
[Boiling point ]

118-130 °C(Press: 25 Torr)
[density ]

0.899±0.06 g/cm3(Predicted)
[storage temp. ]

2-8°C
[form ]

liquid
[pka]

9.39±0.50(Predicted)
[color ]

Pale yellow
[InChI]

InChI=1S/C11H24ClN/c1-3-5-9-13(10-6-4-2)11-7-8-12/h3-11H2,1-2H3
[InChIKey]

ANLMKUQEPXRMGV-UHFFFAOYSA-N
[SMILES]

C(N(CCCC)CCCCl)CCC
Safety DataBack Directory
[Symbol(GHS) ]


GHS08
[Signal word ]

Danger
[Hazard statements ]

H315-H319-H372-H317-H334-H350
[Precautionary statements ]

P501-P272-P260-P270-P202-P201-P264-P280-P284-P302+P352-P308+P313-P337+P313-P305+P351+P338-P362+P364-P304+P340-P333+P313-P405
[HS Code ]

2921199990
Hazard InformationBack Directory
[Uses]

N-Butyl-N-(3-chloropropyl)butan-1-amine acts as a reagent in the process for the production of dronedarone hydrochloride, an antiarrhythmia drug. Impurity of Butoprozine which is an antiarrhythmic drug.
[Synthesis]

3-(DIBUTYLAMINO)-1-PROPANOL

2050-51-3

N-(3-chloropropyl)dibutylamine

36421-15-5

General procedure for the synthesis of N-(3-chloropropyl)dibutylamine from 3-(dibutylamino)propan-1-ol: 3-(dibutylamino)propan-1-ol (2.230 mmol, 0.418 g) was dissolved in chloroform (5 mL), and thionyl chloride (4.460 mmol, 0.328 mL) was slowly added via syringe. The reaction mixture was stirred under reflux conditions for 7 hours. After completion of the reaction, the reaction mixture was diluted with water and dichloromethane and potassium carbonate (1.2 g) was added. The organic layer was washed sequentially with saturated aqueous sodium bicarbonate (5 mL) and water (5 mL). The organic layer was dried with anhydrous magnesium sulfate, filtered, and the solvent was removed in vacuum to afford N-(3-chloropropyl)dibutylamine as a yellow oil (0.430 g, 94% yield).1H NMR (400 MHz, CDCl3) δ 3.62 (t, J = 6.5 Hz, 1H), 2.55 (t, J = 6.8 Hz, 1H), 2.40 (t, 2H) 1.89 (qi, 1H), 1.48-1.36 (m, 2H), 1.36-1.26 (m, 2H), 0.93 (t, J = 7.3 Hz, 3H).13C NMR (101 MHz, CDCl3) δ 54.02, 51.06, 43.45, 30.61, 29.43, 20.67, 14.05. HRMS (EI+): m/z C11H24NCl calculated value: 205.1597, measured value: 205.1596.

[References]

[1] Chem, 2018, vol. 4, # 3, p. 522 - 532
[2] Chemical and Pharmaceutical Bulletin, 2016, vol. 64, # 8, p. 1149 - 1153
[3] Journal of the American Chemical Society, 1945, vol. 67, p. 1416,1417
[4] Journal of the American Chemical Society, 1941, vol. 63, p. 2435
[5] Journal of the American Chemical Society, 1945, vol. 67, p. 1416,1417
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