Diisopropylethylamine → HCID 63136298, compound

HRID 69907Notes

Reaction equation

HRID 69907 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[CH3:11][C:12]1([C:18]([OH:20])=[O:19])[CH2:17][CH2:16][CH2:15][NH:14][CH2:13]1.CCN(C(C)C)C(C)C>CC(O)C>[CH3:11][C:12]1([C:18]([OH:20])=[O:19])[CH2:17][CH2:16][CH2:15][N:14]([C:2]2[CH:7]=[CH:6][N:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])[CH2:13]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27357814-Chloro-3-nitropyridineHCID 184196953-Methylpiperidine-3-carboxylic acid

Product 1

HCID 63136298HCID 63136298, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
60 °C

Procedure

4-chloro-3-nitropyridine (1.1 eq) was added to a solution of 3-methylpiperidine-3-carboxylic acid (1 eq) and DIEA (3 eq) in iPrOH (0.1 M). The reaction mixture was heated in a 60° C. oil bath for 3 h then concentrated in vacuo. The crude residue was diluted with EtOAc and washed with 1.0 N NaOH. The combined aqueous washes were acidified to pH=4 with 1.0 N HCl and extracted with CH2Cl2. The combined organic phases were dried over anhydrous MgSO4, filtered, and concentrated in vacuo to give 3-methyl-(3-nitropyridin-4-yl)piperidine-3-carboxylic acid. LC/MS (m/z): 266.2 (MH+).

Workup

  1. concentrationthen concentrated in vacuo
  2. additionThe crude residue was diluted with EtOAc
  3. washwashed with 1.0 N NaOH
  4. extractionextracted with CH2Cl2
  5. dry with materialThe combined organic phases were dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cd8e2e88020b46ec997df1a4c964011f
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Reaction notes

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