Potassium Iodide → HCID 68521473, compound

HRID 389714Notes

Reaction equation

HRID 389714 reaction equation
[CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[O:3]1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:26][CH2:27][N:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1>CC#N>[N:28]1([CH2:27][CH2:26][NH:15][C:12]2[CH:13]=[CH:14][C:9]([B:4]3[O:3][C:2]([CH3:16])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]3)=[CH:10][CH:11]=2)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 748271-(2-Chloroethyl)piperidineHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Product 1

HCID 68521473HCID 68521473, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-(2-(piperidin-1-yl)ethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamine was prepared by heating 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamine (0.219 g, 1 mmol), potassium iodide (0.006 g, 0.03 mmol), potassium carbonate (0.060 g, 0.4 mmol) and 1-(2-chloroethyl)-piperidine (0.050 g, 0.3 mmol) in MeCN (2 ml) to 110° C. by microwave irradiation for 10 minutes. The crude reaction was purified by preparative HPLC to give the product as a white solid (0.009 g, 0.027 mmol). LCMS (3) 2.50 min; m/z (ES+) 331.

Workup

  1. customby microwave irradiation for 10 minutes
  2. customThe crude reaction
  3. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-224d903949e445afbef9d40c79a6a798
Source dataset
uspto-grants-2013_02
Patent number
US08378095B2

Reaction notes

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