Piperazine → HCID 58707293, compound

HRID 1910605Notes

Reaction equation

HRID 1910605 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-77e5f4d8849640bfbea1517978500036
Source dataset
uspto-grants-2013_12
Patent number
US08604021B2

Reaction notes

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