Water → HCID 66987744, compound

HRID 333421Notes

Reaction equation

HRID 333421 reaction equation
[CH:1]1([NH:4][CH:5]2[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]2)[CH2:3][CH2:2]1.C(N(CC)CC)C.[C:25](Cl)(=O)[CH2:26][CH3:27].[OH2:30]>C1COCC1>[CH:26]1([CH2:2][CH2:3][C:1]([NH:4][CH:5]2[CH2:6][CH2:7][N:8]([C:11]([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12])[CH2:9][CH2:10]2)=[O:30])[CH2:27][CH2:25]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 2769591tert-Butyl 4-(cyclopropylamino)piperidine-1-carboxylate

Product 1

HCID 66987744HCID 66987744, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.8 g (3.3 mmol) of tert-butyl 4-cyclopropylaminopiperidine-1-carboxylate, 0.48 mL (3.3 mmol) of triethylamine and 0.56 mL (3.3 mmol) of propionyl chloride are dissolved in 50 mL of THF. The reaction medium is stirred for 2 hours at room temperature. The reaction is stopped by adding water and the organic products are then extracted with dichloromethane. The organic phase is dried and then evaporated. The crude product obtained is chromatographed on silica gel (eluent: 6/4 heptane/ethyl acetate). 0.87 g of tert-butyl 4-(cyclopropylpropionylamino)piperidine-1-carboxylate in the form of a colourless oil is obtained in a yield of 89%.

Workup

  1. extractionthe organic products are then extracted with dichloromethane
  2. customThe organic phase is dried
  3. customevaporated
  4. customThe crude product obtained
  5. customis chromatographed on silica gel (eluent: 6/4 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-1de102abcc1d483ab3fa12abd58096c9
Source dataset
uspto-grants-2014_11
Patent number
US08877968B2

Reaction notes

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