Potassium Carbonate → HCID 67128562, compound

HRID 403109Notes

Reaction equation

HRID 403109 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[CH:16][CH:15]=[CH:14][C:4]=1[CH2:5][NH:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1.[Br:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]Br.C(=O)([O-])[O-].[K+].[K+]>CC#N>[Br:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][N:6]([CH2:5][C:4]1[CH:14]=[CH:15][CH:16]=[CH:17][C:3]=1[O:2][CH3:1])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123681,6-DibromohexaneHCID 791885N-(2-Methoxybenzyl)-1-(pyridin-2-yl)methanamine

Product 1

HCID 67128562HCID 67128562, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Compound 1 (0.3 g, 1.3 mmol) was dissolved in 10 mL CH3CN and 1,6-dibromohexane (4.85 g, 19 mmol), and potassium carbonate (0.37 g, 2.6 mmol) was added. The reaction mixture stirred overnight at room temperature. The solvent was evaporated to a minimum volume and purified by silica gel chromatography eluting with 100% CH2Cl2 twice and several times with 0.5% methanolic NH3 (7 M NH3 in methanol)/99.5% CH. The organic layers were combined and rotovaped (61.5%). 1H NMR (CDCl3) δ 8.480 (d, 1H, Ar), 7.612 (t, 1H, Ar), 7.553 (d, 1H, Ar), 7.474 (d, 1H, Ar), 7.192 (t, 1H, Ar), 7.097 (t, 1H, Ar), 6.923 (t, 1H, Ar), 6.824 (d, 1H, Ar), 3.776 (overlapped s, 5H, —CH2—, —OCH3), 3.671 (s, 2H, —CH2—), 3.328 (m, 2H, —CH2—), 2.488 (ddd, 2H, —CH2—), 1.783 (p, 2H, —CH2—), 1.531 (m, 2H, —CH2—), 1.331 (p, 2H, —CH2—), 1.271 (p, 2H, —CH2—). Mass Spect=391.14 (M+H)+.

Workup

  1. customThe solvent was evaporated to a minimum volume
  2. custompurified by silica gel chromatography
  3. washeluting with 100% CH2Cl2 twice

Sources & evidence

ORD record
ord-30a168851f2744c9b5083d7fb01d2b3a
Source dataset
uspto-grants-2014_06
Patent number
US08747810B2

Reaction notes

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