Hydrochloric Acid → HCID 67059991, compound

HRID 238282Notes

Reaction equation

HRID 238282 reaction equation
N[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:16])[CH3:15])[CH2:10][CH2:9]1.N([O-])=O.[Na+].[ClH:21]>O.[Cu]Cl>[Cl:21][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:16])[CH3:15])[CH2:10][CH2:9]1

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 23668193Sodium NitriteHCID 67059966HCID 67059966, compound

Product 1

HCID 67059991HCID 67059991, compound

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

1-[4-(2-Amino-phenyl)-piperidin-1-yl]-ethanone (0.3 g, 1.38 mmol) was dissolved in a solution of hydrochloric acid (6 N, 6 mL) and cooled to 0° C. A solution of sodium nitrite (0.097 g, 1.4 mmol) in water (1 mL) was added drop wise and the mixture stirred for 1 hour. The resulting solution was added drop wise to a solution of copper (I) chloride (0.35 g, 3.5 mmol) in hydrochloric acid (6 N, 6 mL). The mixture was allowed to warm to room temperature, and was then diluted with water (20 mL) and the products extracted into ethyl acetate. The organic solution was washed with water (20 mL) then dried over magnesium sulphate, filtered and the solvent removed by evaporation under vacuum to give the title compound as an orange oil (0.2 g). LCMS m/z 238.2 [M+H]+. R.T.=4.30 min (Analytical Method 4).

Workup

  1. temperatureto warm to room temperature
  2. extractionthe products extracted into ethyl acetate
  3. washThe organic solution was washed with water (20 mL)
  4. dry with materialthen dried over magnesium sulphate
  5. filtrationfiltered
  6. customthe solvent removed by evaporation under vacuum

Sources & evidence

ORD record
ord-eb082fa7e0374f369463be11d1a9735c
Source dataset
uspto-grants-2014_02
Patent number
US08642621B2

Reaction notes

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