Hydrogen Bromide → 1-(4-bromophenyl)-N,N-dimethylpiperidine-4-carboxamide

HRID 57576Notes

Reaction equation

HRID 57576 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([C:14]([N:16]([CH3:18])[CH3:17])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.N([O-])=O.[Na+].[BrH:23]>O>[Br:23][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([C:14]([N:16]([CH3:18])[CH3:17])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 260Hydrogen Bromide2×HCID 23668193Sodium NitriteHCID 393499181-(4-aminophenyl)-N,N-dimethylpiperidine-4-carboxamide

Product 1

HCID 711135061-(4-bromophenyl)-N,N-dimethylpiperidine-4-carboxamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

A solution of 1-(4-aminophenyl)-N,N-dimethylpiperidine-4-carboxamide (4.2 g, 16.98 mmol) in 25 mL HBr in 20 mL of water was added a solution of NaNO2 (1.17 g, 16.98 mmol) in water (2 mL) slowly. The mixture was stirred at −10° C.˜0° C. for 30 minutes, and added dropwise to a solution of CuBr (1.34 g, 9.34 mmol) in 12 mL HBr in water (10 mL). Then the mixture was stirred at reflux for 2 hours. The mixture was partitioned between 2N NaOH and EA, washed with EA, dried over Na2SO4. The volatiles were removed in vacuo, and the residue was purified by chromatography with PE/EA (15:1˜2:1) to give 2.5 g of 1-(4-bromophenyl)-N,N-dimethylpiperidine-4-carboxamide.

Workup

  1. stirringThen the mixture was stirred
  2. temperatureat reflux for 2 hours
  3. customThe mixture was partitioned between 2N NaOH and EA
  4. washwashed with EA
  5. dry with materialdried over Na2SO4
  6. customThe volatiles were removed in vacuo
  7. customthe residue was purified by chromatography with PE/EA (15:1˜2:1)

Sources & evidence

ORD record
ord-1528ee19e0514ee0afcd01db614359ef
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Reaction notes

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