Hydrochloric Acid → 6-(Piperidin-4-yl)nicotinonitrile hydrochloride

HRID 874950Notes

Reaction equation

HRID 874950 reaction equation
[ClH:1].[C:2]([C:4]1[CH:5]=[CH:6][C:7]([CH:10]2[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][CH2:11]2)=[N:8][CH:9]=1)#[N:3]>>[ClH:1].[NH:13]1[CH2:12][CH2:11][CH:10]([C:7]2[CH:6]=[CH:5][C:4]([C:2]#[N:3])=[CH:9][N:8]=2)[CH2:15][CH2:14]1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 69453251Tert-butyl 4-(5-cyanopyridin-2-yl)piperidine-1-carboxylate

Product 1

HCID 673246076-(Piperidin-4-yl)nicotinonitrile hydrochloride

Conditions

Temperature
90 °C

Procedure

6N HCl (1.0 mL) was added to tert-butyl 4-(5-cyanopyridin-2-yl)piperidine-1-carboxylate (150 mg, 0.52 mmol) and the reaction mixture was stirred at 90° C. for 30 min, cooled to room temperature, and concentrated under reduced pressure. The crude residue was triturated with ether to afford 6-(piperidin-4-yl)nicotinonitrile hydrochloride (90 mg, crude). 1H NMR (300 MHz, D2O) δ 8.90 (d, J=0.7 Hz, 1H), 8.30 (dd, J=8.2 Hz, 1.9 Hz, 1H), 7.66 (d, J=8.1 Hz, 1H), 3.60-3.55 (m, 2H), 3.27-3.13 (m, 3H), 2.20 (m, 2H), 2.07-1.97 (m, 2H). MS (ESI) m/z: Calculated for C11H13N3: 187.11. found: 188.2 (M+H)+

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. customThe crude residue was triturated with ether

Sources & evidence

ORD record
ord-3dce674109334a53bd147fd52f1f742a
Source dataset
uspto-grants-2015_03
Patent number
US08981084B2

Reaction notes

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