Piperazine → HCID 58707329, compound

HRID 2426041Notes

Reaction equation

HRID 2426041 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([S:23]([CH3:26])(=[O:25])=[O:24])=[C:6]([NH:8][CH:9]2[C:18]3[C:13](=[C:14]([O:21][CH3:22])[CH:15]=[CH:16][C:17]=3[O:19][CH3:20])[CH2:12][CH2:11][CH2:10]2)[CH:7]=1.[NH:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1.C(N(CC)C(C)C)(C)C>C(#N)C>[CH3:22][O:21][C:14]1[CH:15]=[CH:16][C:17]([O:19][CH3:20])=[C:18]2[C:13]=1[CH2:12][CH2:11][CH2:10][CH:9]2[NH:8][C:6]1[CH:7]=[C:2]([N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)[CH:3]=[CH:4][C:5]=1[S:23]([CH3:26])(=[O:25])=[O:24]

Participants

5

Reactant 3

HCID 4837PiperazineHCID 81531DiisopropylethylamineHCID 58707347HCID 58707347, compound

Product 1

HCID 58707329HCID 58707329, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of N-(5-fluoro-2-(methylsulfonyl)phenyl)-1,2,3,4-tetrahydro-5,8-dimethoxynaphthalen-1-amine (1.234 g, 3.26 mmol), piperazine (5.63 g, 65.1 mmol) and N,N-diisopropylethylamine (5.7 mL, 32.6 mmol) in acetonitrile (20 mL) was stirred at reflux for 16 h. The reaction mixture was cooled down and concentrated under reduced pressure. The residue was taken up in dichloromethane, washed with water, dried and concentrated in vacuo to yield 1.04 g of the crude aniline. The crude product was purified by PTLC (20% ethyl acetate in hexanes) to yield 610 mg (42%) of 1,2,3,4-tetrahydro-5,8-dimethoxy-N-(2-(methylsulfonyl)-5-(piperazin-1-yl)phenyl)naphthalen-1-amine: 1H NMR (400 MHz, CD3OD): δ 7.49 (d, 1H), 6.81 (d, 1H), 6.76 (d, 1H), 6.38-6.36 (m, 2H), 5.98 (d, 1H), 4.80 (br s, 1H), 3.79 (s, 3H), 3.67 (s, 3H), 3.37-3.32 (m, 4H), 2.98-2.92 (m, 1H), 2.88-2.82 (m, 7H), 2.44-2.36 (m, 1H), 2.20 (br d, 1H0, 1.86-1.58 (m, 3H). MS (ESI) m/z: Calculated: 445.20; Observed: 446.2 (M++1).

Workup

  1. temperatureat reflux for 16 h
  2. temperatureThe reaction mixture was cooled down
  3. concentrationconcentrated under reduced pressure
  4. washwashed with water
  5. customdried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-12e3461d761e4b03803c35cbb9b27988
Source dataset
uspto-grants-2011_06
Patent number
US07968538B2

Reaction notes

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