Piperazine → HCID 21081974, compound

HRID 970509Notes

Reaction equation

HRID 970509 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([F:12])[CH:10]=2)[N:5]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[C:4](=[O:21])[C:3]=1[C:22]#[N:23].[NH:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1>ClCCl>[F:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)[C:4](=[O:21])[C:3]([C:22]#[N:23])=[C:2]2[N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 21081960HCID 21081960, compound

Product 1

HCID 21081974HCID 21081974, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of Compound 46 (2.0 g, 6.04 mmol) in dichloromethane was added slowly to a stirred solution of piperazine (1.56 g, 18.21 mmol) in dichloromethane at room temperature. The solution was stirred overnight at room temperature. The solvent was removed under reduced pressure. The residue was taken in water, sonicated briefly, and filtered. The solids were dissolved in ethyl acetate and washed by water. The organic layer was dried over Na2SO4 and concentrated to yield 2.18 g (95%) yellow solids. M.P. 240° C. 1H NMR (DMSO-d6): δ 2.84 (s, 1H), 2.94 (m, 4H), 3.54 (m, 4H), 5.45 (s, 2H), 7.15 (m, 2H), 7.27 (m, 2H), 7.44 (dd, J=4.4, 9.3 Hz, 1H), 7.53 (td, J=2.4, 8.0 Hz, 1H), 7.58 (dd, J=2.9, 8.9 Hz, 1H). EIMS m/z 381 (M+1).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customsonicated briefly
  3. filtrationfiltered
  4. dissolutionThe solids were dissolved in ethyl acetate
  5. washwashed by water
  6. dry with materialThe organic layer was dried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8981c94a3a62453bb38e92f08532117a
Source dataset
uspto-grants-2007_12
Patent number
US07312220B2

Reaction notes

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