Triethylamine → N-(9-Acridinyl)-4-(7-hydroxyheptyl)-aniline

HRID 852825Notes

Reaction equation

HRID 852825 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1.CCN(CC)CC.Cl[C:24]1[C:25]2[C:30]([N:31]=[C:32]3[C:37]=1[CH:36]=[CH:35][CH:34]=[CH:33]3)=[CH:29][CH:28]=[CH:27][CH:26]=2>CO>[CH:26]1[C:25]2[C:30](=[N:31][C:32]3[C:37]([C:24]=2[NH:13][C:12]2[CH:11]=[CH:10][C:9]([CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][OH:1])=[CH:15][CH:14]=2)=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 710139-ChloroacridineHCID 226477964-(7-Hydroxyheptyl)-aniline

Product 1

HCID 22647817N-(9-Acridinyl)-4-(7-hydroxyheptyl)-anilineYield 91.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 636.9 mg (3.07 mmol) of 4-(7-hydroxyheptyl)-aniline 30 and 428 μL (3.07 mmol) of Et3N in 20 mL of MeOH were added 656.4 mg (3.07 mmol) of 9-chloroacridine. After stirring for 7 hr at room temperature, the solvent was evaporated. Purification by column chromatography on silica gel with 5% MeOH in CH2Cl2 gave 1.079 g (91%) of N-(9-acridinyl)-4-(7-hydroxyheptyl)-aniline 31: 1H NMR (300 MHz, CDCl3, TMS) δ 8.0-7.9 (m, 4H), 7.63 (t, J=7 Hz, 2H), 7.3-7.2 (m, 2H), 7.07 (d, J=8.3 Hz, 2H), 6.85 (d, J=8.3 Hz, 2H), 3.64 (t, J=6.6 Hz, 2H), 2.57 (t, J=7.6 Hz, 2H), 1.7-1.5 (m, 4H), 1.4-1.3 (m, 6H).

Workup

  1. customthe solvent was evaporated
  2. customPurification by column chromatography on silica gel with 5% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-e36ee000be0b460eb54914f6f2e1d579
Source dataset
uspto-grants-2007_08
Patent number
US07253207B2

Reaction notes

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