Ethyl 4-piperidinecarboxylate → HCID 59845591, compound

HRID 1253836Notes

Reaction equation

HRID 1253836 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N:9]2[C:13]3=[N:14][C:15]([CH3:26])=[CH:16][C:17](OS(C(F)(F)F)(=O)=O)=[C:12]3[C:11]([CH3:27])=[CH:10]2)=[C:4]([CH3:28])[CH:3]=1.[NH:29]1[CH2:39][CH2:38][CH:32]([C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH2:31][CH2:30]1.C(N(CC)C(C)C)(C)C>O>[CH2:36]([O:35][C:33]([CH:32]1[CH2:38][CH2:39][N:29]([C:17]2[CH:16]=[C:15]([CH3:26])[N:14]=[C:13]3[N:9]([C:5]4[C:4]([CH3:28])=[CH:3][C:2]([Cl:1])=[CH:7][C:6]=4[CH3:8])[CH:10]=[C:11]([CH3:27])[C:12]=23)[CH2:30][CH2:31]1)=[O:34])[CH3:37]

Participants

5

Reactant 3

HCID 70770Ethyl 4-piperidinecarboxylateHCID 81531DiisopropylethylamineHCID 86600702HCID 86600702, compound

Product 1

HCID 59845591HCID 59845591, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of the crude trifluoromethanesulfonic acid 1-(4-chloro-2,6-dimethylphenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl ester (20.5 g), ethyl isonipecotate (74.4 g) and N,N-diisopropylethylamine (12.2 g) was heated at 150-170° C. for 1 hour. To the reaction mixture, water was added and extracted with ethyl acetate. The organic layer was washed with water, and brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: hexane/ethyl acetate=5:1) to give 1-[1-(4-chloro-2,6-dimethylphenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]piperidine-4-carboxylic acid ethyl ester (16.6 g) as a pale yellow solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water, and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: hexane/ethyl acetate=5:1)

Sources & evidence

ORD record
ord-a6a41f1a13ad48b0a19945acae8e4b17
Source dataset
uspto-grants-2013_06
Patent number
US08455511B2

Reaction notes

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