Sodium ethoxide → HCID 69673503, compound

HRID 2276340Notes

Reaction equation

HRID 2276340 reaction equation
C([O-])C.[Na+].[O:5]=[C:6]([C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=1)[CH2:7][N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C:9]1=[N:14][C:15]#[N:16]>C(O)C>[NH2:16][C:15]1[N:14]=[C:9]2[CH2:10][CH2:11][CH2:12][CH2:13][N:8]2[C:7]=1[C:6]([C:17]1[CH:18]=[CH:19][C:20]([CH3:23])=[CH:21][CH:22]=1)=[O:5]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 86696593HCID 86696593, compound

Product 1

HCID 69673503HCID 69673503, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium ethanolate (2.44 mL; 6.55 mmol) was added to a solution of N-(1-(2-oxo-2-p-tolylethyl)piperidin-2-ylidene)cyanamide (1.52 g; 5.95 mmol) in dry ethanol (36 mL) under a nitrogen atmosphere and the reaction mixture was heated at reflux for 30 min. After cooling, the volatiles were removed under reduced pressure and the crude residue was purified by flash-chromatography on silica gel using a gradient of methanol (1-10%) in dichloromethane to afford 1.04 g (68%) of (2-amino-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-3-yl)(p-tolyl)methanone as a brownish solid. ESI/APCI(+): 256 (M+H). 1H NMR (DMSO-d6): δ 7.35 (m, 4H, Harom.); 5.63 (bs, 2H, NH2); 3.64 (m, 2H, CH2); 2.66 (m, 2H, CH2); 2.36 (s, 3H, CH3); 1.74 (m, 4H, 2×CH2).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 30 min
  3. temperatureAfter cooling
  4. customthe volatiles were removed under reduced pressure
  5. customthe crude residue was purified by flash-chromatography on silica gel using a gradient of methanol (1-10%) in dichloromethane

Sources & evidence

ORD record
ord-2984481326614da3acb034c8bcdb5ad8
Source dataset
uspto-grants-2015_09
Patent number
US09132129B2

Reaction notes

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