Hydrochloric Acid → N(3-Aminopropyl)-N3-cyclopentadecylpropane-1,3-diamine

HRID 1776961Notes

Reaction equation

HRID 1776961 reaction equation
C(OC([NH:8][CH2:9][CH2:10][CH2:11][N:12]([CH2:20][CH2:21][CH2:22][NH:23][CH:24]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)C(=O)OC(C)(C)C)=O)(C)(C)C.Cl>CCO>[NH2:8][CH2:9][CH2:10][CH2:11][NH:12][CH2:20][CH2:21][CH2:22][NH:23][CH:24]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131734761HCID 131734761, compound

Product 1

HCID 90675689N(3-Aminopropyl)-N3-cyclopentadecylpropane-1,3-diamineYield 134.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Compound 50a (450 mg, 0.8 mmol) was first dissolved in EtOH (60 mL) and stirred at 0° C. for 10 min A 4 M HCl solution (35 mL, 140 mmol) was then added dropwise and stirred for 30 min at 0° C. under N2. The reaction was then slowly warmed to room temperature and stirred under N2 for 4 h. Upon completion, the solvent was removed in vacuo to give 46a as a white solid (365 mg, 98%)1H NMR (D2O) δ 3.25 (m, 1H), 3.15 (t, 6H), 3.10 (t, 2H), 2.09 (m, 4H), 1.72 (m, 4H), 1.39-1.35 (m, 26H); 13C (D2O) δ. HRMS (FAB) m/z calc for C21H45N3 (M+H)+ 340.3613. found 340.3693. Elemental Analysis: C21H48Cl3N3.0.05 H2O theory C, 55.57; H, 10.68; N, 9.26. found C, 55.77; H, 10.65; N, 8.98.

Workup

  1. additionwas then added dropwise
  2. temperatureThe reaction was then slowly warmed to room temperature
  3. stirringstirred under N2 for 4 h
  4. customUpon completion, the solvent was removed in vacuo

Sources & evidence

ORD record
ord-dcebe1b7d05146559c9c49312f184715
Source dataset
uspto-grants-2016_02
Patent number
US09266815B2

Reaction notes

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