Hydrochloric Acid → HCID 66711152, compound

HRID 1262344Notes

Reaction equation

HRID 1262344 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]2[CH2:13][CH2:14][NH:15][CH2:16][CH:17]=2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].Cl.[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][N:29]([C:32](=[O:35])[CH2:33]Br)[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20].C(=O)([O-])[O-].[Cs+].[Cs+].C(#N)C>O>[C:19]([O:23][C:24]([N:26]1[CH2:27][CH2:28][N:29]([C:32](=[O:35])[CH2:33][N:15]2[CH2:14][CH:13]=[C:12]([C:5]3[CH:6]=[CH:7][C:8]([N+:9]([O-:11])=[O:10])=[C:3]([O:2][CH3:1])[CH:4]=3)[CH2:17][CH2:16]2)[CH2:30][CH2:31]1)=[O:25])([CH3:22])([CH3:20])[CH3:21]

Participants

7

Reactant 5

HCID 313Hydrochloric Acid2×HCID 6342AcetonitrileHCID 10796Cesium carbonateHCID 15829155tert-Butyl 4-(bromoacetyl)piperazine-1-carboxylateHCID 569460604-(3-Methoxy-4-nitrophenyl)-1,2,3,6-tetrahydropyridine

Product 1

HCID 66711152HCID 66711152, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a 1-Neck round-bottom flask was added 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 450 mg of BOC precursor for 1 h), 4-(2-Bromo-acetyl)-piperazine-1-carboxylic acid tert-butyl ester (413.0 mg, 1.345 mmol) and cesium carbonate (1095 mg, 3.362 mmol) in acetonitrile (10 mL, 200 mmol). The reaction was stirred overnight at reflux. The reaction mixture was cooled to RT, diluted with water and was extracted (twice) from EtOAc. Combined organic was washed with brine and was dried over MgSO4. After solvent evaporation and flash chromatography (ISCO, EtOAC: MeOH 98:2), the product, 4-{2-[4-(3-Methoxy-4-nitro-phenyl)-3,6-dihydro-2H-pyridin-1-yl]-acetyl}-piperazine-1-carboxylic acid tert-butyl ester, was isolated as a gum/solid (301 mg, 49%). NMR 1H (DMSO-d6)-7.86 (d, 1H, J=8.54 Hz), 7.29 (s, 1H), 7.17 (d, 1H, J=8.58 Hz), 6.44 (s, 1H), 3.96 (s, 3H), 3.52 (br s, 2H), 3.44 (br s, 2H), 3.32 m with the water peak, 8H), 3.30 (m, 2H).

Workup

  1. temperatureat reflux
  2. extractionwas extracted (twice) from EtOAc
  3. washCombined organic was washed with brine
  4. dry with materialwas dried over MgSO4
  5. customAfter solvent evaporation and flash chromatography (ISCO, EtOAC: MeOH 98:2)

Sources & evidence

ORD record
ord-03cb50772eba403ca75741bede0a0275
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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