Piperidine → HCID 66765592, compound

HRID 594997Notes

Reaction equation

HRID 594997 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][N:7]([CH2:9][CH2:10][C:11]([OH:13])=O)[CH:8]=1)([O-:3])=[O:2].C(N(C(C)C)CC)(C)C.[NH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC.C(=O)(O)[O-].[Na+]>CN(C=O)C>[N+:1]([C:4]1[CH:5]=[N:6][N:7]([CH2:9][CH2:10][C:11]([N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[O:13])[CH:8]=1)([O-:3])=[O:2]

Participants

8

Reactant 6

HCID 8082PiperidineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 12298674-Nitro-1H-pyrazole-1-propanoic acid

Product 1

HCID 66765592HCID 66765592, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(4-nitro-1H-pyrazol-1-yl)propanoic acid (4.4 mmol) in 5 mL DMF were added diisopropylethylamine (1.2 mL, 1.5 eq), piperidine (0.66 mL, 1.5 eq), 1-hydroxybenzotriazole (0.90 g, 1.5 eq) and N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide (1.27 g, 1.5 eq). After stirring at rt for 17 h, saturated sodium bicarbonate was added and the aqueous phase extracted with DCM. The combined organic phases were dried over sodium sulfate and evaporated to afford 3-(4-nitro-1H-pyrazol-1-yl)-1-(piperidin-1-yl)propan-1-one in quantitative yield.

Workup

  1. extractionthe aqueous phase extracted with DCM
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-019f609dd6874b6bacc03b0088f177d0
Source dataset
uspto-grants-2016_01
Patent number
US09242987B2

Reaction notes

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