1,2-Dichloroethane → 1-(1-Methyl-cyclopropanecarbonyl)-piperidine-4-carboxylic acid ethyl ester

HRID 2191104Notes

Reaction equation

HRID 2191104 reaction equation
[CH3:1][C:2]1([C:5]([OH:7])=O)[CH2:4][CH2:3]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC.[CH2:29]([O:31][C:32]([CH:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1)=[O:33])[CH3:30]>C(Cl)Cl>[CH2:29]([O:31][C:32]([CH:34]1[CH2:39][CH2:38][N:37]([C:5]([C:2]2([CH3:1])[CH2:4][CH2:3]2)=[O:7])[CH2:36][CH2:35]1)=[O:33])[CH3:30]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 70770Ethyl 4-piperidinecarboxylateHCID 757711-HydroxybenzotriazoleHCID 813261-Methylcyclopropanecarboxylic acid

Product 1

HCID 594381441-(1-Methyl-cyclopropanecarbonyl)-piperidine-4-carboxylic acid ethyl esterYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 14.4 g (0.144 mol) 1-methyl-cyclopropanecarboxylic acid in 200 mL DCM was added 27.1 g (0.141 mol) EDC, 19.10 g (0.141 g) HOBt and 35.93 mL (0.259 mol) Et3N. After 1 h at room temperature 18.9 g (0.12 mol) piperidine-4-carboxylic acid ethyl ester was added and the mixture was stirred at room temperature over night. The mixture was poured onto water and extracted with DCM. The combined organic phases were dried over Na2SO4 and concentrated under vacuum. Column chromatography (SiO2, EtOAc/H, 1:1) yielded 26.1 g (92%) of the title compound as a light yellow oil.

Workup

  1. additionThe mixture was poured onto water
  2. extractionextracted with DCM
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-22c4336baba541adbeb8d3556cf60fc3
Source dataset
uspto-grants-2012_12
Patent number
US08324248B2

Reaction notes

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