N,N-Dimethylglycine → HCID 57470854, compound

HRID 2066162Notes

Reaction equation

HRID 2066162 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:15][N:16]([CH3:21])[CH2:17][C:18](O)=[O:19].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[OH-].[Na+]>CN(C)C=O.[Cl-].[Na+].O.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:7])[NH:8][CH:9]1[CH2:10][CH2:11][N:12]([C:18](=[O:19])[CH2:17][N:16]([CH3:21])[CH3:15])[CH2:13][CH2:14]1)([CH3:4])([CH3:2])[CH3:3]

Participants

9

Reactant 5

HCID 673N,N-DimethylglycineHCID 14798Sodium HydroxideHCID 757711-HydroxybenzotriazoleHCID 7238334-(N-Boc-amino)piperidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 57470854HCID 57470854, compoundYield 112.7%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 4-(tert-butoxycarbonylamino)piperidine (5.0 g) in N,N-dimethylformamide (70 ml) were added N,N-dimethylglycine (2.97 g), 1-hydroxybenzotriazole (3.89 g) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (5.27 g), followed by stirring under a nitrogen atmosphere at room temperature for 46 hr. To the reaction mixture were added ethyl acetate (400 ml), brine (200 ml) and a 1N aqueous solution of sodium hydroxide (50 ml), followed by stirring at room temperature for 30 min and liquid-liquid separation was carried out. The aqueous layer was extracted with ethyl acetate. The organic layer was collected, washed with a 1N aqueous solution of sodium hydroxide and brine in this order, and dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure to provide the titled compound as colorless crystals (8.03 g, quantitative).

Workup

  1. stirringby stirring at room temperature for 30 min
  2. customliquid-liquid separation
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. customThe organic layer was collected
  5. washwashed with a 1N aqueous solution of sodium hydroxide and brine in this order
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-250113d4e15b4edba95ce075c3ec870e
Source dataset
uspto-grants-2012_10
Patent number
US08288538B2

Reaction notes

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