Piperidine → HCID 23108312, compound

HRID 2380771Notes

Reaction equation

HRID 2380771 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. Fog 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. customFog 24 hours
  2. extractionthe resulting mixture is extracted three times with chloroform
  3. washThe organic layer is washed with 10% hydrochloric acid
  4. dry with materiala saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate
  5. distillationAfter the solvent is distilled away under reduced pressure
  6. customthe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-33066712eb4d4db8a40659289cebd0b7
Source dataset
uspto-grants-2012_09
Patent number
US08257943B2

Reaction notes

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