1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 6-(4-Biphenylylmethoxy)-N-(2-piperidinoethyl)nicotinamide

HRID 1356468Notes

Reaction equation

HRID 1356468 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.[C:10]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:15]=[CH:14][C:13]([CH2:16][O:17][C:18]2[CH:26]=[CH:25][C:21]([C:22](O)=[O:23])=[CH:20][N:19]=2)=[CH:12][CH:11]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>C(#N)C.C(=O)([O-])[O-].[K+].[K+].C(N(CC)CC)C.C1COCC1>[C:10]1([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:15]=[CH:14][C:13]([CH2:16][O:17][C:18]2[CH:26]=[CH:25][C:21]([C:22]([NH:1][CH2:2][CH2:3][N:4]3[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]3)=[O:23])=[CH:20][N:19]=2)=[CH:12][CH:11]=1

Participants

9

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 33944N-(2-Aminoethyl)piperidineHCID 757711-HydroxybenzotriazoleHCID 178174806-(4-Biphenylylmethoxy)nicotinic Acid

Product 1

HCID 185083446-(4-Biphenylylmethoxy)-N-(2-piperidinoethyl)nicotinamideYield 66.1%

Reagents, catalysts & solvents 4

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 11430Potassium CarbonateSolvent

Procedure

To a solution of 1-(2-aminoethyl)piperidine (260 mg) in acetonitrile (5 ml)/THF (10 ml) were added 6-(4-biphenylylmethoxy)nicotinic acid (500 mg), WSC (380 mg), HOBt (260 mg), and triethylamine (0.7 ml) at room temperature. After stirring at room temperature for 36 hr, the reaction mixture was diluted with 5% aqueous potassium carbonate and extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride sequentially, dried, and concentrated. The residue was purified by alumina column chromatography (THF) and recrystallized from ethyl acetate to obtain the titled compound (450 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated aqueous sodium chloride sequentially
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by alumina column chromatography (THF)
  6. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-48d9ef30a4504ecbb83fa0f4c8e5be50
Source dataset
uspto-grants-2003_07
Patent number
US06586475B1

Reaction notes

Loading…