2-Bromopyridine → 4-Piperidinecarboxylic acid, 1-(2-pyridinyl)-, ethyl ester

HRID 2118009Notes

Reaction equation

HRID 2118009 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1.[CH2:14]([O:16][C:17](=[O:24])[CH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)[CH3:15]>CC(O)C>[CH2:14]([O:16][C:17]([CH:18]1[CH2:19][CH2:20][N:21]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH2:22][CH2:23]1)=[O:24])[CH3:15]

Participants

5

Reactant 3

HCID 79732-BromopyridineHCID 11430Potassium CarbonateHCID 70770Ethyl 4-piperidinecarboxylate

Product 1

HCID 38156184-Piperidinecarboxylic acid, 1-(2-pyridinyl)-, ethyl ester

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
120 °C

Procedure

Potassium carbonate (52.5 g, 0.379 mol) was charged to a stirred solution of 2-Bromopyridine (60 g, 0.379 mol) and Ethylisonipecotate (59.7 g, 0.379 mol), at an ambient temperature before heating to 120° C. for 24 hours. The mixture was cooled to room temperature and propan-2-ol charged to the solution. The reaction mixture was then filtered and telescoped into preparation 1c.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationThe reaction mixture was then filtered
  3. customtelescoped into preparation 1c

Sources & evidence

ORD record
ord-6a5a0eac86c24267bea133bb3b7389cb
Source dataset
uspto-grants-2008_10
Patent number
US07442795B2

Reaction notes

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