Potassium Carbonate → HCID 60696590, compound

HRID 1025440Notes

Reaction equation

HRID 1025440 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([NH2:10])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]>CN(C=O)C>[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([NH:10][CH2:18][CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrateHCID 31633331-(Propan-2-yl)piperidin-4-amine

Product 1

HCID 60696590HCID 60696590, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Under an argon atmosphere, to a mixed liquid of 1.06 g of 1-isopropylpiperidin-4-amine, 1.00 g of potassium carbonate, and 5.0 mL of DMF was added dropwise a mixture of 0.70 g of ethyl 4-bromobutyrate and 2.0 mL of DMF under ice-cooling, followed by washing with 3.0 mL of DMF. After stirring at room temperature for 96 hours, the reaction mixture was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (aqueous ammonia-methanol-chloroform) to obtain 0.47 g of ethyl 4-[(1-isopropylpiperidin-4-yl)amino]butyrate as a yellow oily substance.

Workup

  1. temperaturecooling
  2. washby washing with 3.0 mL of DMF
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (aqueous ammonia-methanol-chloroform)

Sources & evidence

ORD record
ord-24523133b6b74f6785e810e1809f1e43
Source dataset
uspto-grants-2014_05
Patent number
US08729068B2

Reaction notes

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