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

HRID 393880Notes

Reaction equation

HRID 393880 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). N-(9-acridinyl)-4-(7-iodoheptyl)-aniline (32). To a solution of 604.1 mg (1.57 mmol) of N-(9-acridinyl)-4-(7-hydroxyheptyl)-aniline 31 in 20 mL of pyridine cooled to 0° C. was added 200 μL (2.58 mmol) of methanesulfonyl chloride. The reaction mixture was stirred at 0° C. for 1 hr 20 min, then partitioned between 180 mL of CH2Cl2 and 75 mL of water. The aqueous phase was extracted with CH2Cl2 (3×30 mL). The CH2Cl2 extracts were combined, washed with 40 mL of saturated NaCl solution, dried with MgSO4, and evaporated to dryness.

Workup

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

Sources & evidence

ORD record
ord-399c21d14d7f49378a1ca72f5477dd17
Source dataset
uspto-grants-2004_10
Patent number
US06809176B2

Reaction notes

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