Potassium Carbonate → HCID 86758646, compound

HRID 2298059Notes

Reaction equation

HRID 2298059 reaction equation
Br[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([Cl:24])=[C:7]([CH:23]=1)[C:8]([NH:10][CH2:11][CH2:12][C:13]12[CH2:22][CH:17]3[CH2:18][CH:19]([CH2:21][CH:15]([CH2:16]3)[CH2:14]1)[CH2:20]2)=[O:9].[C:25]([O:29][C:30]([N:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1)=[O:31])([CH3:28])([CH3:27])[CH3:26].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.[I-].[K+]>[Cl:24][C:6]1[CH:5]=[CH:4][C:3]([CH2:2][N:35]2[CH2:34][CH2:33][N:32]([C:30]([O:29][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:31])[CH2:37][CH2:36]2)=[CH:23][C:7]=1[C:8]([NH:10][CH2:11][CH2:12][C:13]12[CH2:20][CH:19]3[CH2:18][CH:17]([CH2:16][CH:15]([CH2:21]3)[CH2:14]1)[CH2:22]2)=[O:9]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 21900027HCID 21900027, compound

Product 1

HCID 86758646HCID 86758646, compoundYield 87.1%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 180AcetoneSolvent

Procedure

A mixture 5-(bromomethyl)-2-chloro-N-(2-tricyclo[3.3.1.13,7]dec-1-ylethyl)-benzamide (Example 18a, 0.35 g), 1-tertbutyloxycarbonylpiperazine (0.213 g), potassium carbonate (0.20 g) and potassium iodide (10 mg) in acetone (5 ml) was heated at 60° C. for 2 h. The acetone was removed under vacuum, the residue taken into dichlorometane and the solid removed by filtration. The crude material was purified on a silica gel eluting with dichloromethane/ethanol (0-10% gradient) to afford the subtitle compound as a white foam (0.383 g).

Workup

  1. customThe acetone was removed under vacuum
  2. customthe solid removed by filtration
  3. customThe crude material was purified on a silica gel eluting with dichloromethane/ethanol (0-10% gradient)

Sources & evidence

ORD record
ord-0e6ab99c25cf4fa79fa82c9747b3d22f
Source dataset
uspto-grants-2002_12
Patent number
US06492355B1

Reaction notes

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