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

HRID 632419Notes

Reaction equation

HRID 632419 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-19218380cfe64baa86f6bb8568450f27
Source dataset
uspto-grants-2016_04
Patent number
US09321727B2

Reaction notes

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