Ethyl Bromide → 9-((N-(5-hydroxypentyl)-N-(ethyl)amino)methyl)anthracene

HRID 429706

Reaction equation

HRID 429706 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH:7][CH2:8][C:9]1[C:10]2[C:15]([CH:16]=[C:17]3[C:22]=1[CH:21]=[CH:20][CH:19]=[CH:18]3)=[CH:14][CH:13]=[CH:12][CH:11]=2.C([O-])([O-])=O.[K+].[K+].[CH2:29](Br)[CH3:30]>C(#N)C>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]([CH2:8][C:9]1[C:10]2[C:15]([CH:16]=[C:17]3[C:22]=1[CH:21]=[CH:20][CH:19]=[CH:18]3)=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:29][CH3:30]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 108809079-((5-Hydroxypentyl)aminomethyl)anthracene

Product 1

HCID 226622019-((N-(5-hydroxypentyl)-N-(ethyl)amino)methyl)anthraceneYield 98%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

9-((5-hydroxypentyl)aminomethyl)anthracene (1.00 g, 3.41 mol) and K2CO3 (0.518 g, 3.75 mmol) were taken up in 25 mL acetonitrile. Ethyl bromide (11.14 g, 102 mmol) was added and the mixture was refluxed under nitrogen for 24 h. The mixture was filtered on a sintered-glass frit and the solvent and excess ethyl bromide was removed under reduced pressure. Removal of the solvent afforded 1.07 g (98% yield) of 6 as a yellow solid; 1H NMR (300.13 MHz, CD3CN) δ1.15 (m, 2H), 1.38 (m, 5H), 1.81 (m, 2H), 3.05 (m, 4H), 3.49 (t, 2H), 5.21 (s, 2H), 7.45 (m, 2H), 7.62 (m, 2H), 8.05 (d, 2H), 8.44 (m, 3H); 13C-{1H} NMR (75.4 MHz, CDCl3) δ131.8, 131.3, 130.8, 129.6, 128.0, 125.6, 124.0, 61.7, 53.1, 49.4, 48.7, 31.4, 23.9, 23.3, 10.0.

Workup

  1. temperaturethe mixture was refluxed under nitrogen for 24 h
  2. filtrationThe mixture was filtered on a sintered-glass frit
  3. customthe solvent and excess ethyl bromide was removed under reduced pressure
  4. customRemoval of the solvent

Sources & evidence

ORD record
ord-83dd505ddd544a2fa1374a4e5e365c3b
Source dataset
uspto-grants-2001_11
Patent number
US06319540B1

Linked notes

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