Hydrochloric Acid → 3,N-Dimethyl-4-piperazin-1-yl-benzamide

HRID 1184461Notes

Reaction equation

HRID 1184461 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8](=[O:11])[NH:9][CH3:10])[CH:5]=[CH:4][C:3]=1[N:12]1[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]1.Cl>O1CCOCC1.CCOCC>[CH3:10][NH:9][C:8](=[O:11])[C:6]1[CH:5]=[CH:4][C:3]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[C:2]([CH3:1])[CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59416789Tert-butyl 4-(2-methyl-4-(methylcarbamoyl)phenyl)piperazine-1-carboxylate

Product 1

HCID 287495403,N-Dimethyl-4-piperazin-1-yl-benzamide

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
23 °C

Procedure

To tert-butyl 4-(2-methyl-4-(methylcarbamoyl)phenyl)piperazine-1-carboxylate (1.90 g, 5.70 mmol) was added hydrochloric acid solution (17.10 mL, 68.4 mmol) in dioxane at 23° C. The reaction was stirred at 23° C. for 30 min. The resulting suspension was diluted with Et2O (20 mL), filtered, rinsed with Et2O (3×10 mL), and the resulting solid was dried in vacuo to provide the title compound as an off-white, hygroscopic solid (1.70 g, 5.55 mmol, 97% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.28 (s, 3H) 2.72-2.79 (m, 3H) 3.05-3.14 (m, 4H) 3.17-3.28 (m, 4H) 7.06 (d, J=8.34 Hz, 1H) 7.64-7.68 (m, 1H) 7.68-7.70 (m, 1H) 8.29-8.39 (m, 1H) 9.36 (br. s., 2H). ESI-MS: m/z 234.2 (M+H)+.

Workup

  1. filtrationfiltered
  2. washrinsed with Et2O (3×10 mL)
  3. customthe resulting solid was dried in vacuo

Sources & evidence

ORD record
ord-6af7bf1c280f4b989f118553ef683b84
Source dataset
uspto-grants-2014_03
Patent number
US08669249B2

Reaction notes

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