Piperazine → HCID 21081974, compound

HRID 1767504Notes

Reaction equation

HRID 1767504 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-d025ef9baf2e487cb0dcce2dc2605ddb
Source dataset
uspto-grants-2007_06
Patent number
US07235546B2

Reaction notes

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