Potassium Carbonate → HCID 86722854, compound

HRID 1778758Notes

Reaction equation

HRID 1778758 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=O)=[C:4]([CH2:12]Br)[CH:3]=1.[CH3:14][N:15]1[CH2:20][CH2:19][CH:18]([NH2:21])[CH2:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:10][CH:11]=1)[C:6](=[O:8])[N:21]([CH:18]1[CH2:19][CH2:20][N:15]([CH3:14])[CH2:16][CH2:17]1)[CH2:12]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27375314-Amino-1-methylpiperidineHCID 22031079Methyl 4-bromo-2-(bromomethyl)benzoate

Product 1

HCID 86722854HCID 86722854, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methyl 4-bromo-2-(bromomethyl)benzoate (0.3 g, 1 mmol; AstaTech Cat. No. 27012), 1-methylpiperidin-4-amine (0.14 g, 1.3 mmol)(Combi-blocks Cat. No. 4003460), and potassium carbonate (0.19 g, 1.4 mmol) in ethanol (5 mL) in a sealed reaction vial was stirred at 80° C. for 1 h. After cooling the solid was filtered off. The filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-50%) to afford the desired product (0.1 g). LCMS (M+H)+=309.0/311.0.

Workup

  1. temperatureAfter cooling the solid
  2. filtrationwas filtered off
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-50%)

Sources & evidence

ORD record
ord-f017a9528e804b08acdf23c957f5936a
Source dataset
uspto-grants-2016_02
Patent number
US09266892B2

Reaction notes

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