Hydrochloric Acid → N-cyclopropyl-3-methyl-4-(piperazin-1-yl)benzamide dihydrochloride

HRID 69707Notes

Reaction equation

HRID 69707 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]3)=[C:9]([CH3:26])[CH:8]=2)=[O:6])[CH2:3][CH2:2]1.[ClH:27]>O1CCOCC1.CCOCC>[ClH:27].[ClH:27].[CH:1]1([NH:4][C:5](=[O:6])[C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]3)=[C:9]([CH3:26])[CH:8]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59416795Tert-butyl 4-(4-(cyclopropylcarbamoyl)-2-methylphenyl)piperazine-1-carboxylate

Product 1

HCID 66775049N-cyclopropyl-3-methyl-4-(piperazin-1-yl)benzamide dihydrochlorideYield 100%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
23 °C

Procedure

To tert-butyl 4-(4-(cyclopropylcarbamoyl)-2-methylphenyl)piperazine-1-carboxylate (1.490 g, 4.15 mmol) was added Hydrochloric acid solution (8.72 mL, 34.9 mmol) in dioxane at 23° C. The reaction was stirred at 23° C. for 30 min. The resulting suspension was diluted with Et2O (10 mL), filtered, rinsed with Et2O (3×5 mL), and the resulting solid was dried in vacuo to provide N-cyclopropyl-3-methyl-4-(piperazin-1-yl)benzamide dihydrochloride (1.37 g, 4.15 mmol, 100% yield) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.51-0.61 (m, 2 H) 0.61-0.70 (m, 2 H) 2.28 (s, 3 H) 2.82 (tq, J=7.41, 3.99 Hz, 1 H) 3.02-3.13 (m, 4 H) 3.14-3.29 (m, 4 H) 7.05 (d, J=8.34 Hz, 1 H) 7.62-7.69 (m, 2 H) 8.32 (d, J=4.29 Hz, 1 H) 9.38 (br. s., 2 H). ESI-MS: m/z 260.2 (M+H)+. mp=171.5-172.8° C.

Workup

  1. filtrationfiltered
  2. washrinsed with Et2O (3×5 mL)
  3. customthe resulting solid was dried in vacuo

Sources & evidence

ORD record
ord-4938d6aee1c44308809672196fdbc851
Source dataset
uspto-grants-2014_09
Patent number
US08822470B2

Reaction notes

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