Piperidine → 4-Bromo-2-(piperidin-1-yl)benzaldehyde

HRID 1823115Notes

Reaction equation

HRID 1823115 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4](F)[CH:3]=1.[NH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:3]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 11430Potassium CarbonateHCID 1435174-Bromo-2-fluorobenzaldehyde

Product 1

HCID 221715904-Bromo-2-(piperidin-1-yl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-bromo-2-fluorobenzaldehyde (3.0 g), piperidine (2.93 ml) and potassium carbonate (5.11 g) in N,N-dimethylformamide (30 ml) was stirred at 100° C. for 12 hours. The mixture was cooled to room temperature. The mixture was partitioned between ethyl acetate and water. The organic layer was separated, washed with water, saturated aqueous ammonium chloride solution and brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=9/1) to give 4-bromo-2-(1-piperidinyl)benzaldehyde (3.5 g).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customThe mixture was partitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. washwashed with water, saturated aqueous ammonium chloride solution and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-7ffed40fb3c5428483a2ba54b9afbad7
Source dataset
uspto-grants-2006_05
Patent number
US07037938B2

Reaction notes

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