1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 68455440, compound

HRID 502355Notes

Reaction equation

HRID 502355 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH:10]([NH2:13])[CH2:9][CH2:8]2)=[CH:4][C:3]=1[O:16][CH2:17][CH3:18].[NH2:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](O)=[O:25])=[CH:22][N:21]=1.CCN=C=NCCCN(C)C.C([O-])(O)=O.[Na+]>CN(C=O)C>[NH2:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([NH:13][CH:10]2[CH2:11][CH2:12][N:7]([CH2:6][C:5]3[CH:14]=[CH:15][C:2]([Cl:1])=[C:3]([O:16][CH2:17][CH3:18])[CH:4]=3)[CH2:8][CH2:9]2)=[O:25])=[CH:22][N:21]=1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 184966-Aminonicotinic acidHCID 516892Sodium BicarbonateHCID 592103771-(4-Chloro-3-ethoxybenzyl)piperidin-4-ylamine

Product 1

HCID 68455440HCID 68455440, compoundYield 30.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

1-(4-Chloro-3-ethoxy-benzyl)piperidin-4-ylamine (0.33 g, 1.0 mmol), 6-amino-nicotinic acid (0.17 g, 1.0 mmol) and EDCI (0.28 g, 1.2 mmol) were mixed with DMF (5 ml) and heated to 60° C. for 24 h, after which time the reaction was allowed to cool, poured into dilute NaHCO3 and extracted with EtOAc. The combined organic was dried (Na2SO4) and concentrated. The residue was purified by flash column chromatography (DCM:MeOH 9:1-4:1) affording the title product (0.12 g, 24%).

Workup

  1. temperatureto cool
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic was dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatography (DCM:MeOH 9:1-4:1)

Sources & evidence

ORD record
ord-a4bba37de29d4014a3d82612daf8c2f2
Source dataset
uspto-grants-2010_08
Patent number
US07772253B2

Reaction notes

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