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

HRID 559314Notes

Reaction equation

HRID 559314 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 1-methyl-cyclopropanecarboxylic acid (14.4 g, 0.144 mol) in 200 mL of CH2Cl2 was added (27.10 g, 0.141 mol) of EDC, (19.10 g, 0.141 g) of HOBt and Et3N (35.93 mL, 0.259 mol). After one hour at RT, was added piperidine-4-carboxylic acid ethyl ester (18.90 g, 0.120 mol). The mixture was stirred at RT over night and then poured onto water and extracted with CH2Cl2. The combined organic phases were dried over Na2SO4 and concentrated under vacuo. Column chromatography (SiO2, EtOAc/H, 1:1) yielded 26.1 g (92%) of the title compound as a light yellow oil.

Workup

  1. additionpoured onto water
  2. extractionextracted with CH2Cl2
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. concentrationconcentrated under vacuo

Sources & evidence

ORD record
ord-0add6833c1a040a8b5c19116fc7df9fa
Source dataset
uspto-grants-2011_11
Patent number
US08063075B2

Reaction notes

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