Potassium Iodide → HCID 18381502, compound

HRID 2298091Notes

Reaction equation

HRID 2298091 reaction equation
[Br:1][C:2]1[CH:21]=[CH:20][C:19]([CH2:22]Br)=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:5].[C:24]([O:28][C:29]([N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1)=[O:30])([CH3:27])([CH3:26])[CH3:25].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O>[CH3:20][CH2:21][CH2:2][CH:3]([CH3:18])[CH3:4].[Br:1][C:2]1[CH:21]=[CH:20][C:19]([CH2:22][N:34]2[CH2:33][CH2:32][N:31]([C:29]([O:28][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:30])[CH2:36][CH2:35]2)=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:15][CH:14]3[CH2:16][CH:10]([CH2:11][CH:12]([CH2:13]3)[CH2:17]1)[CH2:9]2)=[O:5]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 18381501HCID 18381501, compound

Product 2

HCID 78922-MethylpentaneHCID 18381502HCID 18381502, compoundYield 151.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-bromo-5-bromomethyl-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (Example 65a, 5.0 g), 1-tertbutyloxycarbonylpiperazine (2.3 g), potassium carbonate (3.2 g), potassium iodide (0.30 g) and acetone (75 ml) was refluxed in the dark for 14 h. The mixture was concentrated in vacuo, partitioned between ethyl acetate and water, then washed with brine. The organic layer was dried over magnesium sulfate and concentrated in vacuo. Recrystallization from ethyl acetate:isohexane gave the subtitle compound as colourless solid (4.7 g).

Workup

  1. temperaturewas refluxed in the dark for 14 h
  2. concentrationThe mixture was concentrated in vacuo
  3. custompartitioned between ethyl acetate and water
  4. washwashed with brine
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-c29ecfba811e49b4a1b7f9084f916343
Source dataset
uspto-grants-2002_12
Patent number
US06492355B1

Reaction notes

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