Hydrochloric Acid → 11-Amino-1-piperzin-1-yl-undecane-1-one dihydrochloride salt

HRID 2420745Notes

Reaction equation

HRID 2420745 reaction equation
[ClH:1].C(OC([N:9]1[CH2:14][CH2:13][N:12]([C:15](=[O:34])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26]C(OC(C)(C)C)=O)[CH2:11][CH2:10]1)=O)(C)(C)C>O1CCOCC1.ClCCl>[ClH:1].[ClH:1].[NH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][C:15]([N:12]1[CH2:13][CH2:14][NH:9][CH2:10][CH2:11]1)=[O:34]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 672149744-(11-tert-Butoxycarbonylaminoundecanoyl)piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 6721559411-Amino-1-piperzin-1-yl-undecane-1-one dihydrochloride salt

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 7 (204 mg, 0.43 mmol) in dichloromethane (3 mL) which had been pre-cooled to 0° C. The reaction was allowed to warm to ambient temperature, stirred for 2 hours, and the solvent then removed under vacuum. Recrystallization from methanol and diethyl ether produced salt 8 (123 mg, 84%) as a white solid: 1H NMR (300 MHz, CD3OD) δ 1.34 (s, 12H), 1.58-1.66 (m, 4H), 2.43 (t, 2H, J=7.4 Hz), 2.90 (t, 2H, J=7.5 Hz), 3.20-3.28 (m, 4H), 3.78-3.83 (m, 4H); m/z (ESI) 270 [C15H31N3O+H]+.

Workup

  1. temperatureto warm to ambient temperature
  2. customthe solvent then removed under vacuum
  3. customRecrystallization from methanol and diethyl ether produced salt 8 (123 mg, 84%) as a white solid

Sources & evidence

ORD record
ord-0299b0a9df70470ca7f7db7bd47764ce
Source dataset
uspto-grants-2011_06
Patent number
US07956059B2

Reaction notes

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