Piperazine → HCID 58707293, compound

HRID 2426047Notes

Reaction equation

HRID 2426047 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH2:7][CH2:6][CH:5]2[NH:12][C:13]1[CH:18]=[C:17](F)[CH:16]=[CH:15][C:14]=1[S:20]([CH3:23])(=[O:22])=[O:21].[NH:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.C(N(CC)C(C)C)(C)C>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH2:7][CH2:6][CH:5]2[NH:12][C:13]1[CH:18]=[C:17]([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[CH:16]=[CH:15][C:14]=1[S:20]([CH3:23])(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 4837PiperazineHCID 81531DiisopropylethylamineHCID 58707330HCID 58707330, compound

Product 1

HCID 58707293HCID 58707293, compoundYield 15.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 6-chloro-N-(5-fluoro-2-(methylsulfonyl)phenyl)chroman-4-amine (143.0 mg, 0.4 mmol), piperazine (694.0 mg, 8.00 mmol) and N,N-diisopropylethylamine (0.52 mL, 4.00 mmol) in acetonitrile (5 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. The crude product was purified by silica chromatography (5% methanol in dichloromethane) to yield 26.0 mg (15% yield) of desired product. 1H NMR (400 MHz, CD3OD): δ 7.64 (d, 1H) 7.25 (d, 1H), 7.15 (dd, 1H), 6.81 (d, 1H), 6.45 (d, 1H), 6.35 (dd, 1H), 6.20 (d, 1H), 4.65 (m, 1H), 4.26 (m, 2H), 3.31 (m, 4H), 3.03 (m, 4H), 2.98 (s, 3H), 2.18 (m, 2H).

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
  7. customThe crude product was purified by silica chromatography (5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-755ed88d1dbc4df4aa70a2f03d244803
Source dataset
uspto-grants-2011_06
Patent number
US07968538B2

Reaction notes

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