Hydrochloric Acid → HCID 63372946, compound

HRID 2407184Notes

Reaction equation

HRID 2407184 reaction equation
Cl.[Br:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9]N.[CH3:11][N:12]1[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]1.Cl>C(O)(=O)C>[Br:2][C:3]1[C:4]2[NH:9][C:15]3[CH2:16][CH2:17][N:12]([CH3:11])[CH2:13][C:14]=3[C:5]=2[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 740491-Methyl-4-piperidoneHCID 27239122-Bromophenylhydrazine hydrochloride

Product 1

HCID 63372946HCID 63372946, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of (2-bromophenyl)hydrazine hydrochloride (1.1 g, 4.92 mmol; Aldrich) and 1-methyl-4-piperidone (0.56 g, 4.92 mmol; Aldrich) was combined with a solution of HCl in acetic acid (1.0 M, 30 mL; Aldrich) and stirred at 70° C. for 18 hours in a sealed tube. The reaction mixture was concentrated under vacuum. The residue was taken up in toluene (100 mL) and concentrated under vacuum to remove most of the acetic acid (the azeotrope procedure was repeated a second time). The residue was dissolved in dimethyl sulfoxide (20 mL) and purified by reverse-phase HPLC [Waters XBridge™ RP18 column, 5 μm, 50×100 mm, flow rate 100 mL/minute, 50-99% gradient of methanol in buffer (0.1 M aqueous ammonium bicarbonate, adjusted to pH 10 with ammonium hydroxide)] to afford the title compound: 1H NMR (400 MHz, methanol-d4) δ ppm 2.54 (s, 3H), 2.85-2.90 (m, 2H), 2.93-2.98 (m, 2H), 3.66 (t, J=1.5 Hz, 2H), 6.88 (t, J=7.8 Hz, 1H), 7.19 (dd, J=7.8, 0.8 Hz, 1H), 7.32 (dd, J=7.8, 0.8 Hz, 1H); MS (DCI) m/z 265/267 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. concentrationconcentrated under vacuum
  3. customto remove most of the acetic acid (the azeotrope procedure
  4. dissolutionThe residue was dissolved in dimethyl sulfoxide (20 mL)
  5. custompurified by reverse-phase HPLC [Waters XBridge™ RP18 column, 5 μm, 50×100 mm, flow rate 100 mL/minute, 50-99% gradient of methanol in buffer (0.1 M aqueous ammonium bicarbonate, adjusted to pH 10 with ammonium hydroxide)]

Sources & evidence

ORD record
ord-603fbcbabd2a4c98aa742d22fca7f2b4
Source dataset
uspto-grants-2014_08
Patent number
US08809532B2

Reaction notes

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