Hydrochloric Acid → HCID 66711550, compound

HRID 1262343Notes

Reaction equation

HRID 1262343 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]([C:13]2[CH2:14][CH2:15][NH:16][CH2:17][CH:18]=2)[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11].Cl.Br[CH:21]([CH3:25])[C:22]([NH2:24])=[O:23].C(=O)([O-])[O-].[Cs+].[Cs+].C(#N)C>>[CH3:2][O:3][C:4]1[CH:5]=[C:6]([C:13]2[CH2:18][CH2:17][N:16]([CH:21]([CH3:25])[C:22]([NH2:24])=[O:23])[CH2:15][CH:14]=2)[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 10796Cesium carbonateHCID 1011182-BromopropanamideHCID 574161654-(3-Methoxy-4-nitrophenyl)-1,2,3,6-tetrahydropyridine--hydrogen chloride (1/1)

Product 1

HCID 66711550HCID 66711550, compound

Procedure

A mixture of 4-(3-Methoxy-4-nitro-phenyl)-1,2,3,6-tetrahydro-pyridine hydrochloride (364 mg, 1.34 mmol) (generated by 4N HCl treatment of the of BOC precursor, 450 mg, for 1 h), 2-Bromo-propionamide (204 mg, 1.34 mmol), and cesium carbonate (1095 mg, 3.362 mmol) in acetonitrile (10 mL, 200 mmol) was stirred overnight at reflux. The mixture was cooled to RT and was filtered through a pad of celite. After solvent evaporation and flash chromatography (ISCO, EtOAC: MeOH 98:3), the product, 2-[4-(3-Methoxy-4-nitro-phenyl)-3,6-dihydro-2H-pyridin-1-yl]-propionamide was isolated as a gum (101 mg, 25%). MS: 306 (M+H).

Workup

  1. temperatureat reflux
  2. filtrationwas filtered through a pad of celite
  3. customAfter solvent evaporation and flash chromatography (ISCO, EtOAC: MeOH 98:3)

Sources & evidence

ORD record
ord-fa415fa57eda4eab8e0cd7d8877017da
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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