N,N'-Dimethylethylenediamine → cis-1-[4-(Octahydro-quinoline-1-carbonyl)-thiophen-2-yl]-piperazin-2-one

HRID 1809097Notes

Reaction equation

HRID 1809097 reaction equation
Br[C:2]1[S:6][CH:5]=[C:4]([C:7]([N:9]2[C@@H:18]3[C@@H:13]([CH2:14][CH2:15][CH2:16][CH2:17]3)[CH2:12][CH2:11][CH2:10]2)=[O:8])[CH:3]=1.[NH:19]1[CH2:24][CH2:23][NH:22][CH2:21][C:20]1=[O:25].C(=O)([O-])[O-].[K+].[K+].CNCCNC>COCCOC.C(Cl)Cl.[Cu]I>[N:9]1([C:7]([C:4]2[CH:3]=[C:2]([N:19]3[CH2:24][CH2:23][NH:22][CH2:21][C:20]3=[O:25])[S:6][CH:5]=2)=[O:8])[C@@H:18]2[C@@H:13]([CH2:14][CH2:15][CH2:16][CH2:17]2)[CH2:12][CH2:11][CH2:10]1

Participants

8

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 231360Piperazin-2-oneHCID 86646712HCID 86646712, compound

Product 1

HCID 86646713cis-1-[4-(Octahydro-quinoline-1-carbonyl)-thiophen-2-yl]-piperazin-2-oneYield 61.4%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
120 °C

Procedure

cis-(5-Bromo-thiophen-3-yl)-(octahydro-quinolin-1-yl)-methanone (0.05 g, 0.15 mmol) was dissolved in DME (1 mL) and piperazin-2-one (0.3 mmol), potassium carbonate (0.15 mmol), copper (I) iodide (0.003 g) and dimethylethylenediamine (0.0013 g) were added. The mixture was heated to 120° C. for 65 hours. The mixture was diluted with DCM (10 mL) and the organic solution washed with water, then evaporated to give a brown oil. The residue was purified by flash chromatography on silica, eluting with 0-40% methanol in DCM. The fractions containing the desired product were combined and evaporated to give the title compound as a pale brown oil (0.032 g). LCMS m/z 348.05 [M+H]+ RT=6.24 min (Analytical Method 2). 1H NMR δ (ppm)(CHCl3-d): 7.0 (s, 1H), 6.7 (s, 1H), 4.6 (m, 1H), 4.0-3.6 (m, 5H), 3.3 (m, 2H), 3.0 (m, 1H), 2.0-1.0 (m, 16H).

Workup

  1. washthe organic solution washed with water
  2. customevaporated
  3. customto give a brown oil
  4. customThe residue was purified by flash chromatography on silica
  5. washeluting with 0-40% methanol in DCM
  6. additionThe fractions containing the desired product
  7. customevaporated

Sources & evidence

ORD record
ord-b533e2314bad439e8bd5d1d6e309ec8c
Source dataset
uspto-grants-2013_01
Patent number
US08362008B2

Reaction notes

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