4-Acetamidopiperidine → HCID 49431041, compound

HRID 874952Notes

Reaction equation

HRID 874952 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1.[C:10]([NH:13][CH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)(=[O:12])[CH3:11]>C(O)CC(C)C>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([N:17]2[CH2:18][CH2:19][CH:14]([NH:13][C:10](=[O:12])[CH3:11])[CH2:15][CH2:16]2)=[N:3][CH:4]=1)#[N:7]

Participants

4

Reactant 2

HCID 14451564-AcetamidopiperidineHCID 51520946-Chloro-3-pyridinecarbonitrile

Product 1

HCID 49431041HCID 49431041, compoundYield 58.5%

Reagents, catalysts & solvents 1

HCID 31260Isoamyl AlcoholSolvent

Conditions

Temperature
140 °C

Procedure

6-Chloronicotinonitrile (300 mg, 2.1 mmol) and 4-acetylaminopiperidine (610 mg, 4.33 mmol) were taken in isoamyl alcohol (15 mL) and the mixture was heated to 140° C. for 2 h. Reaction mixture was cooled to room temperature and the solvent was evaporated under reduced pressure. The crude product was purified by column chromatography (silica gel 60-120 mesh, eluent 5% MeOH in CHCl3) to afford N-(1-(5-cyanopyridin-2-yl)piperidin-4-yl)acetamide (300 mg, yield 57%) as white solid. 1H NMR (400 MHz, DMSO-d6) δ 8.47 (d, J=2.4 Hz, 1H), 7.83-7.80 (m, 2H), 6.95 (d, J=9.3 Hz, 1H), 4.32-4.28 (m, 2H), 3.89-3.80 (m, 1H), 3.14-3.07 (m, 2H), 1.80 (m, 2H), 1.78 (s, 3H), 1.33-1.24 (m, 2H). MS (ESI) m/z: Calculated for C13H16N4O: 244.13. found: 245.2 (M+H)+

Workup

  1. customReaction mixture
  2. temperaturewas cooled to room temperature
  3. customthe solvent was evaporated under reduced pressure
  4. customThe crude product was purified by column chromatography (silica gel 60-120 mesh, eluent 5% MeOH in CHCl3)

Sources & evidence

ORD record
ord-fa6dfe0c5a29444da2abf27a9f3b786b
Source dataset
uspto-grants-2015_03
Patent number
US08981084B2

Reaction notes

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