Potassium Iodide → HCID 67661919, compound

HRID 399432Notes

Reaction equation

HRID 399432 reaction equation
Br[CH2:2][CH2:3][N:4]1[C:8]([C:9]([O:11]C)=O)=[CH:7][C:6]([C:13]([O:15][CH3:16])=[O:14])=[N:5]1.C(N(C(C)C)CC)(C)C.[C:26]([N:33]1[CH2:38][CH2:37][CH:36]([CH2:39][CH2:40][NH2:41])[CH2:35][CH2:34]1)([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27].[I-].[K+]>CC#N>[CH3:16][O:15][C:13]([C:6]1[CH:7]=[C:8]2[C:9](=[O:11])[N:41]([CH2:40][CH2:39][CH:36]3[CH2:35][CH2:34][N:33]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:38][CH2:37]3)[CH2:2][CH2:3][N:4]2[N:5]=1)=[O:14]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 81531DiisopropylethylamineHCID 1484510Dimethyl 1-(2-bromoethyl)-1H-pyrazole-3,5-dicarboxylateHCID 1514258tert-Butyl 4-(2-aminoethyl)piperidine-1-carboxylate

Product 1

HCID 67661919HCID 67661919, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 3-2 (14.0 g, 48.0 mmol), diisopropylethyl amine (25 ml, 144 mmol), Boc-4-aminoethylpiperidine (12.0 g, 52.6 mmol), and potassium iodide (2.39 g, 0.3 mmol) in 250 ml CH3CN was refluxed under N2 for 4.5 h then cooled, filtered and evaporated at reduced pressure. The resulting yellow residue was chromatographed on silica gel using EtOAc as eluent to give 3-3 as an off-white crystalline solid.

Workup

  1. temperaturethen cooled
  2. filtrationfiltered
  3. customevaporated at reduced pressure
  4. customThe resulting yellow residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-ebb972f759d446a28838b3d6fdf12e20
Source dataset
uspto-grants-1998_10
Patent number
US05821241

Reaction notes

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