Hydrogen Bromide → HCID 71093693, compound

HRID 57555Notes

Reaction equation

HRID 57555 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([N:14]([CH3:18])[C:15](=[O:17])[CH3:16])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.N([O-])=O.[Na+].[OH-].[Na+].[BrH:25]>O>[Br:25][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([N:14]([CH3:18])[C:15](=[O:17])[CH3:16])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 260Hydrogen Bromide2×HCID 14798Sodium HydroxideHCID 23668193Sodium NitriteHCID 53930420N-(1-(4-aminophenyl)piperidin-4-yl)-N-methylacetamide

Product 1

HCID 71093693HCID 71093693, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N-(1-(4-aminophenyl)piperidin-4-yl)-N-methylacetamide (479.7 mg, 1.94 mmol) in 6 mL of aq HBr was added a solution of NaNO2 (147 mg, 2.13 mmol) in 2 mL of H2O at 0° C., then the mixture was stirred at 0° C. for 40 minutes. After that, the mixture was poured into a solution of CuBr (584 mg, 4.07 mmol) in 6 mL aq HBr at 0° C., the reaction was heated to 60° C. and stirred for 2 hours. After cooling, the mixture was based with 2M NaOH to pH=8-9 and extracted with EA, washed with H2O and brine, dried and concentrated to give black solid. MS (m/z): 313 (M+H)+

Workup

  1. temperaturethe reaction was heated to 60° C.
  2. stirringstirred for 2 hours
  3. temperatureAfter cooling
  4. extractionextracted with EA
  5. washwashed with H2O and brine
  6. customdried
  7. concentrationconcentrated
  8. customto give black solid

Sources & evidence

ORD record
ord-8ac06cddeb4444e38498d4f5b8caaad2
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Reaction notes

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