N,N'-Dimethylethylenediamine → HCID 69359054, compound

HRID 852661Notes

Reaction equation

HRID 852661 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:12](=[C:13](I)[CH:14]=1)[NH:11][CH:10]=[C:9]2[CH2:16][CH3:17])=[O:5])[CH3:2].[NH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][C:19]1=[O:24].[O-]P([O-])([O-])=O.[K+].[K+].[K+].CNCCNC>C1(C)C=CC=CC=1.[Cu]I>[CH2:16]([C:9]1[C:8]2[C:12](=[C:13]([N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][C:19]3=[O:24])[CH:14]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:7]=2)[NH:11][CH:10]=1)[CH3:17]

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 126652-PiperidoneHCID 62657Potassium Phosphate, TribasicHCID 69357900Ethyl 3-ethyl-7-iodo-1H-indole-5-carboxylate

Product 1

HCID 69359054HCID 69359054, compoundYield 27.3%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of ethyl 3-ethyl-7-iodo-1H-indole-5-carboxylate (D190) (1 g, 2.91 mmol, 1 equiv) in toluene (10 ml) were added 2-piperidinone (346 mg, 3.50 mmol, 1.2 equiv), K3PO4 (1.24 g, 5.83 mmol, 2 equiv), CuI (56 mg, 0.29 mmol, 0.1 equiv) and dimethyl ethylene diamine (62 μl, 0.58 mmol, 0.2 equiv) and the resulting mixture was stirred at 100° C. for 15 h then cooled to room temperature and concentrated in vacuo. The residue was partitioned between AcOEt and H2O and the layers were separated. The organic phase was dried under MgSO4 and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (AcOEt/iso-hexane: 1/0) gave ethyl 3-ethyl-7-(2-oxo-1-piperidinyl)-1H-indole-5-carboxylate (B165) (250 mg, 27%) as an off-white solid. [M+H]+=315.4, RT=2.98 min.

Workup

  1. temperaturethen cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between AcOEt and H2O
  4. customthe layers were separated
  5. customThe organic phase was dried under MgSO4
  6. concentrationconcentrated in vacuo
  7. customPurification of the residue by flash chromatography on silica gel (AcOEt/iso-hexane: 1/0)

Sources & evidence

ORD record
ord-f1325bdc72c44df9875ac3704089edd5
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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