Hydrochloric Acid → HCID 67323555, compound

HRID 874936Notes

Reaction equation

HRID 874936 reaction equation
Cl.[C:2]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH:15]([CH3:16])[CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][CH:11]2[CH3:24])=[N:8][CH:9]=1)#[N:3]>>[CH3:16][CH:15]1[CH2:14][NH:13][CH2:12][CH:11]([CH3:24])[N:10]1[C:7]1[CH:6]=[CH:5][C:4]([C:2]#[N:3])=[CH:9][N:8]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 69935615HCID 69935615, compound

Product 1

HCID 67323555HCID 67323555, compoundYield 112.5%

Conditions

Temperature
90 °C

Procedure

6N HCl (0.5 mL) was added to tert-butyl 4-(5-cyanopyridin-2-yl)-3,5-dimethylpiperazine-1-carboxylate (120 mg, 0.37 mmol) and the reaction mixture was stirred at 90° C. for 30 min. the reaction mixture was cooled to room temperature. The reaction mixture was concentrated under reduced pressure and triturated with ether to afford 6-(2,6-dimethylpiperazin-1-yl)nicotinonitrile (90 mg, crude), which was carried through without further purification. 1H NMR (300 MHz, D2O) δ 8.51 (d, J=2.2 Hz, 1H), 7.93 (dd, J=9.1 Hz, J=2.3 Hz, 1H), 6.97 (d, J=9.2 Hz, 1H), 4.75 (m, 2H), 3.53-3.49 (m, 2H), 3.41-3.34 (m, 2H), 1.42 (s, 3H), 1.39 (s, 3H).

Workup

  1. temperaturewas cooled to room temperature
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customtriturated with ether

Sources & evidence

ORD record
ord-633d512db62646f6b5d73314d5b4115c
Source dataset
uspto-grants-2015_03
Patent number
US08981084B2

Reaction notes

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