Aniline → 1,1-Dimethylethyl 3-[(phenylamino)carbonyl]-1-piperidinecarboxylate

HRID 1246898Notes

Reaction equation

HRID 1246898 reaction equation
[C:1]([N:8]1[CH2:16][CH2:15][CH2:14][CH:10]([C:11]([OH:13])=O)[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl>[C:18]1([NH:17][C:11]([CH:10]2[CH2:14][CH2:15][CH2:16][N:8]([C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])[CH2:9]2)=[O:13])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 10868DicyclohexylcarbodiimideHCID 27356471-((Tert-butoxy)carbonyl)piperidine-3-carboxylic acid

Product 1

HCID 181042161,1-Dimethylethyl 3-[(phenylamino)carbonyl]-1-piperidinecarboxylateYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-Boc-nipecotic acid 33 (102 mg, 0.445 mmol) and aniline (41 μL, 1.0 eq.) in 2 mL of dry CH2Cl2 was added DCC-resin (430 mg). The reaction mixture was shaken at room temperature overnight. Filtration and removal of the solvent gave oily crude product, which was purified by flash column chromatography (silica gel, hexane:ethyl acetate) to afford 1-Boc-piperidine-3-carboxylic acid phenyl amide 34 as a colorless oil (120 mg, 89%).

Workup

  1. filtrationFiltration and removal of the solvent
  2. customgave oily crude product, which
  3. customwas purified by flash column chromatography (silica gel, hexane:ethyl acetate)

Sources & evidence

ORD record
ord-114f13251464455b9939deb12426f4af
Source dataset
uspto-grants-2006_10
Patent number
US07129228B2

Reaction notes

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