Ethyl 4-piperidinecarboxylate → HCID 3422241, compound

HRID 2381179Notes

Reaction equation

HRID 2381179 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].[N:12]1([S:18](Cl)(=[O:20])=[O:19])[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([S:18]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)(=[O:20])=[O:19])[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 70770Ethyl 4-piperidinecarboxylateHCID 12798265Morpholine-4-sulfonyl chloride

Product 1

HCID 3422241HCID 3422241, compoundYield 103.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Piperidine-4-carboxylic acid ethyl ester (0.943 g) dissolved in methylene chloride (60 ml) under an argon atmosphere was treated at RT, first with 4-dimethylaminopyridine (1.465 g) then dropwise with morpholine-4-sulfonyl chloride (1.136 g) and the reaction mixture was stirred for 12 h at RT to complete the reaction. The reaction mixture was then partitioned between methylene chloride and aqueous 1N HCL, the layers were separated and the organic layer washed with 2M aqueous KHCO3 then dried over Na2SO4. The solvent was evaporated off, to give 1-(morpholine-4-sulfonyl)-piperidine-4-carboxylic acid ethyl ester (1.9 g) as a light yellow solid which was directly used in the next step.

Workup

  1. customthe reaction
  2. customThe reaction mixture was then partitioned between methylene chloride and aqueous 1N HCL
  3. customthe layers were separated
  4. washthe organic layer washed with 2M aqueous KHCO3
  5. dry with materialthen dried over Na2SO4
  6. customThe solvent was evaporated off

Sources & evidence

ORD record
ord-c34ee9435c4f4c02b0366ffa1a8b94f0
Source dataset
uspto-grants-2012_09
Patent number
US08258158B2

Reaction notes

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