1,2-Dichloroethane → Ethyl 1-(1-(4-chlorobenzyl)-1H-pyrrole-2-carbonyl)piperidine-4-carboxylate

HRID 83594Notes

Reaction equation

HRID 83594 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][N:7]2[CH:11]=[CH:10][CH:9]=[C:8]2[C:12]([OH:14])=O)=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[NH:40]1[CH2:45][CH2:44][CH:43]([C:46]([O:48][CH2:49][CH3:50])=[O:47])[CH2:42][CH2:41]1>CCOCC.CCOC(C)=O.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH:11]=[CH:10][CH:9]=[C:8]2[C:12]([N:40]2[CH2:45][CH2:44][CH:43]([C:46]([O:48][CH2:49][CH3:50])=[O:47])[CH2:42][CH2:41]2)=[O:14])=[CH:15][CH:16]=1

Participants

9

Reactant 5

HCID 111,2-DichloroethaneHCID 70770Ethyl 4-piperidinecarboxylateHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 41200551-[(4-chlorophenyl)methyl]-1H-pyrrole-2-carboxylic acid

Product 1

HCID 68380169Ethyl 1-(1-(4-chlorobenzyl)-1H-pyrrole-2-carbonyl)piperidine-4-carboxylateYield 75.8%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The following was added sequentially to anhydrous DMF (6 mL): 1-(4-chlorobenzyl)-1H-pyrrole-2-carboxylic acid (175 mg, 0.743 mmol), Hunig's Base (389 μl, 2.228 mmol), EDC (157 mg, 0.817 mmol), HOBT (125 mg, 0.817 mmol), and finally ethyl piperidine-4-carboxylate (172 μl, 1.114 mmol). The reaction was allowed to stir at room temperature for 24 h. At this time, a 1:1 solution of EtOAc:Et2O (100 mL) was added and washed with 10% Na2CO3 (2×50 mL) and brine (1×50 mL). The organic solution was then dried with anhydrous MgSO4 and concentrated in vacuo. Material was purified by column chromatography (20 g silica, 20% EtOAc/Hexanes) to provide 211 mg of the title compound.

Workup

  1. washwashed with 10% Na2CO3 (2×50 mL) and brine (1×50 mL)
  2. dry with materialThe organic solution was then dried with anhydrous MgSO4
  3. concentrationconcentrated in vacuo
  4. customMaterial was purified by column chromatography (20 g silica, 20% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-3e196f0b53984b56b8a57f9cace36026
Source dataset
uspto-grants-2014_09
Patent number
US08846684B2

Reaction notes

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