Triethylamine → Naphthylacridine

HRID 393883Notes

Reaction equation

HRID 393883 reaction equation
CO[C:3]1[CH:4]=[C:5](CCCCCCCCC2C=CC(N)=CC=2)[C:6]2[C:11]([C:12]=1OC)=[CH:10][CH:9]=[CH:8][CH:7]=2.CCN(CC)CC.Cl[C:38]1[C:39]2[C:44]([N:45]=[C:46]3[C:51]=1[CH:50]=[CH:49][CH:48]=[CH:47]3)=[CH:43][CH:42]=[CH:41][CH:40]=2>CO>[C:10]1([C:40]2[C:39]3[C:44](=[N:45][C:46]4[C:51]([CH:38]=3)=[CH:50][CH:49]=[CH:48][CH:47]=4)[CH:43]=[CH:42][CH:41]=2)[C:11]2[C:6](=[CH:5][CH:4]=[CH:3][CH:12]=2)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 710139-ChloroacridineHCID 226477951-(3,4-Dimethoxy-1-naphthyl)-8-(4-aminophenyl)-octane

Product 1

HCID 22647828NaphthylacridineYield 153%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 99 mg (2.53×10−4 mol) of 1-(3,4-dimethoxy-1-naphthyl)-8-(4-aminophenyl)-octane 37 and 35 mL (2.5×10−4 mol) of Et3N in 4 mL of MeOH were added 54 mg (2.53×10−4 mol) of 9-chloroacridine. The reaction mixture was stirred at room temperature for 20 hr. Evaporation of solvent and column chromatography on silica gel with first 1% MeOH in CH2Cl2 and then 3% MeOH in CH2Cl2 afforded 118.2 mg (82%) of acridine 38: 1H NMR (250 MHz, CDCl3, TMS) δ 8.14 (d, J=8 Hz, 1H), 8.0-7.9 (m, 5H), 7.66 (br t, 2H), 7.46 (t, J=8 Hz, 1H), 7.37 (t, J=8 Hz, 1H), 7.3-7.2 (m, 2H), 7.12 (s, 1H), 7.06 (d, J=8.4 Hz, 2H), 6.82 (d, J=8.4 Hz, 2H), 3.1-3.0 (m, 2H), 2.6-2.5 (m, 2H), 1.8-1.3 (m, 12H).

Workup

  1. customEvaporation of solvent and column chromatography on silica gel with first 1% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-80eafc00f95d42a4a96591f7d606b50d
Source dataset
uspto-grants-2004_10
Patent number
US06809176B2

Reaction notes

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