Piperidine → HCID 23108312, compound

HRID 2369755Notes

Reaction equation

HRID 2369755 reaction equation
[C:1]([NH:4][CH:5]([CH3:20])[C:6]([NH:8][C@H:9]([C:17]([OH:19])=O)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])(=[O:3])[CH3:2].Cl.CN(C)CCCN=C=NCC.O[N:34]1[C:38]2C=[CH:40][CH:41]=[CH:42][C:37]=2N=N1.N1CCCCC1>CN(C)C=O.O>[C:1]([NH:4][CH:5]([CH3:20])[C:6]([NH:8][CH:9]([CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:17]([N:34]1[CH2:40][CH2:41][CH2:42][CH2:37][CH2:38]1)=[O:19])=[O:7])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 8082PiperidineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 61137645HCID 61137645, compound

Product 1

HCID 23108312HCID 23108312, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

N-[2-(Acetylamino)propionyl]phenylalanine obtained in Experimental Example 21 (10 mg, 0.036 mmol) is suspended in N,N-dimethylformamide (5 ml), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (14 mg, 0.073 mmol), 1-hydroxybenzotriazole (15 mg, 0.11 mmol) and piperidine (40 μl, 0.40 mmol) are added to the suspension at room temperature, followed by stirring at 50° C. for 24 hours. To the reaction mixture is added water, and the resulting mixture is extracted three times with chloroform. The organic layer is washed with 10% hydrochloric acid and a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. After the solvent is distilled away under reduced pressure, the residue is purified by silica gel column chromatography to obtain 1-{(2-[N-(2-(acetylamino)propionyl)amino]-3-phenylpropionyl}piperidine.

Workup

  1. extractionthe resulting mixture is extracted three times with chloroform
  2. washThe organic layer is washed with 10% hydrochloric acid
  3. dry with materiala saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate
  4. distillationAfter the solvent is distilled away under reduced pressure
  5. customthe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f2d8da02e92f4bca9f13f09a48a5dfc3
Source dataset
uspto-grants-2014_04
Patent number
US08709752B2

Reaction notes

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