Ethyl piperidine-2-carboxylate → HCID 21255125, compound

HRID 636579Notes

Reaction equation

HRID 636579 reaction equation
Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.[NH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH:25]1[C:30]([O:32][CH2:33][CH3:34])=[O:31].[CH3:35][C:36]1[N:44]=[CH:43][CH:42]=[CH:41][C:37]=1[C:38](O)=[O:39]>ClCCl.O.C(N(CC)CC)C>[CH3:35][C:36]1[N:44]=[CH:43][CH:42]=[CH:41][C:37]=1[C:38]([N:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH:25]1[C:30]([O:32][CH2:33][CH3:34])=[O:31])=[O:39]

Participants

8

Reactant 4

HCID 27517Ethyl piperidine-2-carboxylateHCID 6433732-Methylnicotinic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 21255125HCID 21255125, compoundYield 90.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

150.8 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 60.3 g of 1-hydroxybenzotriazole hydrate are added to a suspension of 82.4 g of ethyl piperidine-2-carboxylate in 500 cm3 of dichloromethane. The solution remains milky and 45 g of 2-methylnicotinic acid are added. The solution becomes clear and 161 cm3 of triethylamine are added. The mixture is kept stirred at ambient temperature overnight. The mixture is hydrolysed with 2×1 liter of water. The organic phase is then dried over magnesium sulphate and evaporated at reduced pressure (2.7 kPa). The oil obtained is chromatographed on a column of 8 cm diameter containing 900 g of silica (0.04-0.02). Elution is carried out with ethyl acetate, 70-cm3 fractions being collected. The homogeneous fractions are combined and concentrated at reduced pressure (2.7 kPa). 81.86 g of ethyl N-(2-methylnicotinoyl)piperidine-2-carboxylate are thus obtained in the form of a colourless oil (Rf=0.21; thin layer chromatography on silica gel; ethyl acetate eluent).

Workup

  1. dry with materialThe organic phase is then dried over magnesium sulphate
  2. customevaporated at reduced pressure (2.7 kPa)
  3. customThe oil obtained
  4. customis chromatographed on a column of 8 cm diameter
  5. additioncontaining 900 g of silica (0.04-0.02)
  6. washElution
  7. custombeing collected
  8. concentrationconcentrated at reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-0d82045571604e3dab6ca69e5d9640d6
Source dataset
uspto-grants-2001_02
Patent number
US06194426B1

Reaction notes

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