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

HRID 988777Notes

Reaction equation

HRID 988777 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-22f3080363934b2d8e2d610e47648770
Source dataset
uspto-grants-2003_10
Patent number
US06635661B2

Reaction notes

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