Benzylamine → HCID 22678394, compound

HRID 1837751Notes

Reaction equation

HRID 1837751 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH2:9][N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]2[CH2:16][C:17]([OH:19])=O)=[CH:7][CH:6]=[CH:5][N:4]=1.[CH2:20]([NH2:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.O>[CH2:20]([NH:27][C:17](=[O:19])[CH2:16][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][N:10]1[CH2:9][C:8]1[C:3]([O:2][CH3:1])=[N:4][CH:5]=[CH:6][CH:7]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 22678317HCID 22678317, compound

Product 1

HCID 22678394HCID 22678394, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1.0 g of 2-[1-[(2-Methoxy-3-pyridyl)methyl]-2-piperidyl]acetic acid, 0.41 ml of benzylamine, 950 mg of WSC and 260 mg of HOBt were suspended in DMF, followed by stirring at room temperature for 2 hours. Water was added thereto, and the mixture was extracted with ethyl acetate. The extract was dried over sodium sulfate. The drying agent was filtered off, the solvent was evaporated and the residue was purified by silica gel column chromatography (ethyl acetate:methanol=10:1, subsequently 5:1), to give 500 mg of the title compound as white crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over sodium sulfate
  3. filtrationThe drying agent was filtered off
  4. customthe solvent was evaporated
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate

Sources & evidence

ORD record
ord-612b7d066edb40dea71f1a7f8ea1df8c
Source dataset
uspto-grants-2004_08
Patent number
US06784192B2

Reaction notes

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