Hydrochloric Acid → 2-Cyclopropyl-1-methyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethylamine hydrochloride

HRID 927805Notes

Reaction equation

HRID 927805 reaction equation
C(OC(=O)[NH:7][C:8]([CH3:19])([C:13]1[N:17]=[C:16]([CH3:18])[O:15][N:14]=1)[CH2:9][CH:10]1[CH2:12][CH2:11]1)(C)(C)C.[ClH:21]>CO>[ClH:21].[CH:10]1([CH2:9][C:8]([NH2:7])([CH3:19])[C:13]2[N:17]=[C:16]([CH3:18])[O:15][N:14]=2)[CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 71087718[2-Cyclopropyl-1-methyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 710877902-Cyclopropyl-1-methyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethylamine hydrochlorideYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of [2-cyclopropyl-1-methyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethyl]-carbamic acid tert-butyl ester (0.4 g, 1.43 mmol) in methanol (10 mL) was added hydrochloric acid (4N in dioxane, 3.5 mL, 14.8 mmol) and the reaction mixture was stirred at ambient temperature for 4 hours. The organic layer was washed with brine (20 mL), dried over anhydrous Na2SO4 and concentrated to give the title product (0.25 g, 81%) as a light yellow solid. 1H-NMR (DMSO, 400 MHz): 0.010-0.02 (m, 2H); 0.38-0.42 (m, 2H); 0.61-0.63 (m, 1H); 1.67 (s, 3H); 1.78-1.91 (m, 2H); 2.66 (s, 3H); 8.89 (br s, 3H).

Workup

  1. washThe organic layer was washed with brine (20 mL)
  2. dry with materialdried over anhydrous Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-f20e8fbe93674b318cb4b66f303ad7d8
Source dataset
uspto-grants-2016_03
Patent number
US09290451B2

Reaction notes

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