Dimethylamine → HCID 59509452, compound

HRID 2407515Notes

Reaction equation

HRID 2407515 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([C:19]([OH:21])=O)[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)=[O:5])[CH3:2].ON1C2C=CC=CC=2N=N1.[CH3:32][NH:33][CH3:34].CCN=C=NCCCN(C)C.Cl>O.C1COCC1>[CH2:1]([O:3][C:4]([C:6]1([C:19](=[O:21])[N:33]([CH3:34])[CH3:32])[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66741169HCID 66741169, compound

Product 1

HCID 59509452HCID 59509452, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

THF (5 ml) charged in to a R B flask followed by the addition of piperidine-1,4,4-tricarboxylic acid 1-tert-butyl ester 4-ethyl ester (0.5 g) and 1-hydroxybenzotriazole (0.38 g). Allowed to stir the reaction mixture at 25-300 C for 30 mins. Dimethylamine (0.75 mL) followed by EDC HCl (0.38 g) was added in to the above reaction mixture at 25-300 C. Allowed the reaction mixture to stir at 25-300 C for 1-2 hrs. Reaction is followed by TLC. The reaction mixture concentrated under vacuum using rota vapour and the product slurry obtained is suspended in D M Water (5 mL). The product extracted in to ethyl acetate (2×5 mL). The combined product layer dried with sodium sulphate and concentrated under vacuum to yield crude product which in turn purified by a column chromatography to yield pure 4-dimethylcarbamoyl-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester.

Workup

  1. additionwas added in to the above reaction mixture at 25-300 C
  2. stirringAllowed the reaction mixture to stir at 25-300 C for 1-2 hrs
  3. customReaction
  4. concentrationThe reaction mixture concentrated under vacuum
  5. customthe product slurry obtained
  6. extractionThe product extracted in to ethyl acetate (2×5 mL)
  7. dry with materialThe combined product layer dried with sodium sulphate
  8. concentrationconcentrated under vacuum
  9. customto yield crude product which in turn
  10. custompurified by a column chromatography

Sources & evidence

ORD record
ord-4ff1c8a2986c46999b1addadeeba1fc7
Source dataset
uspto-grants-2014_08
Patent number
US08809539B2

Reaction notes

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