Hydrochloric Acid → 11-Aminoundecanoic acid (3-dimethylaminopropyl)amide dihydrochloride salt

HRID 2420743Notes

Reaction equation

HRID 2420743 reaction equation
[ClH:1].C(OC(=O)[NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19](=[O:27])[NH:20][CH2:21][CH2:22][CH2:23][N:24]([CH3:26])[CH3:25])(C)(C)C>O1CCOCC1.ClCCl>[ClH:1].[ClH:1].[CH3:26][N:24]([CH3:25])[CH2:23][CH2:22][CH2:21][NH:20][C:19](=[O:27])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][NH2:8]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86634233[10-(3-Dimethylaminopropylcarbamoyl)decyl]carbamic acid tert-butyl ester

Product 1

HCID 8663423111-Aminoundecanoic acid (3-dimethylaminopropyl)amide dihydrochloride saltYield 86%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 4.0 M hydrochloric acid in dioxane (1 mL) was added dropwise to a solution of amide 4 (154 mg, 0.40 mmol) in dichloromethane (3 mL) which was pre-cooled to 0° C. After this time, the reaction was then allowed to warm to ambient temperature and stirred for an additional 2 hours. After this time, the solvent was removed under vacuum to give salt 5 (124 mg, 86%) as a white solid: 1H NMR (300 MHz, CD3OD) δ 1.34 (s, 12H), 1.53-1.66 (m, 6H), 1.87-1.98 (m, 2H), 2.19-2.37 (m, 3H), 2.88-2.97 (m, 8H), 3.20-3.28 (m, 2H), 3.28-3.33 (m, 2H); m/z (ESI) 286 [C16H35N3O+H]+.

Workup

  1. temperatureto warm to ambient temperature
  2. customAfter this time, the solvent was removed under vacuum

Sources & evidence

ORD record
ord-ebe2cc95ea4148ab8549cdf9a504cd70
Source dataset
uspto-grants-2011_06
Patent number
US07956059B2

Reaction notes

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