1,2-Dichloroethane → HCID 11348649, compound

HRID 2261394Notes

Reaction equation

HRID 2261394 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].C(Cl)CCl.[CH2:13]([N:20]1[CH2:25][CH2:24][CH:23]=[C:22]([CH2:26][CH2:27][C:28](O)=[O:29])[C:21]1=[O:31])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl.C(OCC)(=O)C>[NH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[NH:8][C:28](=[O:29])[CH2:27][CH2:26][C:22]1[C:21](=[O:31])[N:20]([CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:25][CH2:24][CH:23]=1

Participants

7

Reactant 3

HCID 111,2-DichloroethaneHCID 7243O-PhenylenediamineHCID 11219135HCID 11219135, compound

Product 1

HCID 11348649HCID 11348649, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

40 mg of 1,2-phenylenediamine (0.37 mmol), 77 mg of EDC (0.4 mmol) and 1 mg of DMAP (3 M %) were added to reaction solution dissolving 3-(1-benzyl-2-oxo-1,2,5,6-tetrahydro-pyridin-3-yl)-propionic acid prepared by above Example 8 in 1 ml of methylene chloride under Argon atmosphere. After the mixture was stirred for 13 hrs at room temperature, the resulting mixture was diluted with ethyl acetate and washed with 10% NaOH solution (10 ml). Then the residue was extracted with 50 ml of chloroform, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The resultant was purified by Silica gel column chromatography with a solvent mixture mixed with methanol and chloroform (1:20) as an eluant to give 96 mg of N-(2-amino-phenyl)-3-(1-benzyl-2-oxo-1,2,5,6-tetrahydro-pyridin-3-yl)-propionamide (g2) (yield: 91%).

Workup

  1. washwashed with 10% NaOH solution (10 ml)
  2. extractionThen the residue was extracted with 50 ml of chloroform
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resultant was purified by Silica gel column chromatography with a solvent mixture
  7. additionmixed with methanol and chloroform (1:20) as an eluant

Sources & evidence

ORD record
ord-8a0e5ad5caf44d28ba0ab67b8bf55e1b
Source dataset
uspto-grants-2010_12
Patent number
US07846963B2

Reaction notes

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