1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59318053, compound

HRID 2190567Notes

Reaction equation

HRID 2190567 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:9]=[CH:10][CH:11]=1)[NH2:8])([CH3:4])([CH3:3])[CH3:2].[CH2:12]([O:14][C:15]([CH:17]1[CH2:22][CH2:21][N:20]([C:23]2[CH:28]=[CH:27][C:26]([C:29](O)=[O:30])=[CH:25][CH:24]=2)[CH2:19][CH2:18]1)=[O:16])[CH3:13].CCN=C=NCCCN(C)C>C(Cl)Cl>[CH2:12]([O:14][C:15]([CH:17]1[CH2:18][CH2:19][N:20]([C:23]2[CH:24]=[CH:25][C:26]([C:29](=[O:30])[NH:8][C:7]3[CH:9]=[CH:10][CH:11]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:6]=3)=[CH:27][CH:28]=2)[CH2:21][CH2:22]1)=[O:16])[CH3:13]

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 793343-tert-ButylanilineHCID 190638644-[4-(Ethoxycarbonyl)piperidin-1-YL]benzoic acid

Product 1

HCID 59318053HCID 59318053, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-tert-butyl aniline (54 mg, 0.36 mmol), 1-(4-carboxy-phenyl)-piperidine-4-carboxylic acid ethyl ester (100 mg, 0.36 mmol) and EDCI (200 mg, 1.08 mmol) in CH2Cl2 was stirred at room temperature overnight. Next morning the reaction mixture was partitioned between EtOAc and water. The organic layer was separated dried over Na2SO4, filtered and concentrated. The residue was purified on a silica gel column with 20-50% Et2O in hexanes gradient to afford the product (31 mg; Yield: 21%). HRMS m/z calcd for C25H32N2O3 [M+H]+: 409.2486. Found: 409.2484.

Workup

  1. customNext morning the reaction mixture was partitioned between EtOAc and water
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified on a silica gel column with 20-50% Et2O in hexanes gradient
  7. customto afford the product (31 mg; Yield: 21%)

Sources & evidence

ORD record
ord-bfcdd8cf68034b3bb8c718408aef3bc2
Source dataset
uspto-grants-2012_12
Patent number
US08324385B2

Reaction notes

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