1,2-Dichloroethane → HCID 59716941, compound

HRID 1992724Notes

Reaction equation

HRID 1992724 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:17][CH:18]1[CH2:23][NH:22][CH2:21][CH:20]([CH3:24])[NH:19]1.C(Cl)CCl>CN(C1C=CN=CC=1)C.ClCCl>[CH3:17][CH:18]1[NH:19][CH:20]([CH3:24])[CH2:21][N:22]([C:14]([CH:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:12]2)=[O:16])[CH2:23]1

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 660562,6-DimethylpiperazineHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acid

Product 1

HCID 59716941HCID 59716941, compoundYield 58.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid (2.3 g, 10 mmol), 2,6-dimethylpiperazine (1.14 g, 10 mmol), and EDC (3.82 g, 20 mmol) and DMAP (catalytic) in 20 ml dichloromethane was stirred at room temperature overnight, concentrated, added water and extracted with ethyl acetate 2×50 ml. The combined organic solution was dried over sodium sulfate and concentrated. The residue was applied to flash column chromatography using methylene chloride and methanol (100:5) as eluents to give 1.9 g of desired product.

Workup

  1. concentrationconcentrated
  2. additionadded water
  3. extractionextracted with ethyl acetate 2×50 ml
  4. dry with materialThe combined organic solution was dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4f3541ebed934964bab7643d5658efd9
Source dataset
uspto-grants-2010_01
Patent number
US07649092B2

Reaction notes

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