1,2-Dichloroethane → HCID 13060622, compound

HRID 1068149Notes

Reaction equation

HRID 1068149 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH2:11][CH:12]1[CH2:17][CH2:16][N:15]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:14][CH2:13]1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>C(Cl)Cl>[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:11][CH:12]1[CH2:17][CH2:16][N:15]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:14][CH2:13]1)=[O:6]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 227Anthranilic AcidHCID 757711-HydroxybenzotriazoleHCID 4158521-Benzyl-4-piperidylamine

Product 1

HCID 13060622HCID 13060622, compoundYield 13.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1.0 g 2-aminobenzoic acid and 1.39 g of 4-amino-1-benzylpiperidine in 10 mL of methylene chloride was added 1.18 g of HOBT followed by 2.10 g of EDC. After stirring at rt for 6 hours, the reaction mixture was diluted with methylene chloride. The organic phase was washed with brine and dried over anhydrous MgSO4. Concentration under reduced pressure followed by flash chromatography eluting with 9% EtOAc in hexane, 50% EtOAc in hexane and 10% MeOH in EtOAc afforded 309 mg of the title compound as a viscous oil.

Workup

  1. washThe organic phase was washed with brine
  2. dry with materialdried over anhydrous MgSO4
  3. concentrationConcentration under reduced pressure
  4. washeluting with 9% EtOAc in hexane, 50% EtOAc in hexane

Sources & evidence

ORD record
ord-4937d911d60c40f09c2c2ea3514cc483
Source dataset
uspto-grants-2001_06
Patent number
US06248755B1

Reaction notes

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