Bromoacetonitrile → HCID 22503616, compound

HRID 1251113Notes

Reaction equation

HRID 1251113 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[C:11]([C:19]3[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=3)[N:10]=2)[CH2:5][CH2:4]1)[CH3:2].[H-].[Na+].[H][H].Br[CH2:31][C:32]#[N:33].[Cl-:34].[NH4+]>O1CCCC1.C(OCC)(=O)C>[ClH:34].[C:32]([CH2:31][O:25][C:22]1[CH:21]=[CH:20][C:19]([C:11]2[N:10]=[C:9]([N:6]3[CH2:5][CH2:4][N:3]([CH2:1][CH3:2])[CH2:8][CH2:7]3)[C:18]3[C:13]([CH:12]=2)=[CH:14][CH:15]=[CH:16][CH:17]=3)=[CH:24][CH:23]=1)#[N:33]

Participants

8

Reactant 5

HCID 11534BromoacetonitrileHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 1357190421-(1-Ethylpiperazin-4-yl)-3-(4-hydroxyphenyl)isoquinolineHCID 178418361HCID 178418361, compound

Product 1

HCID 22503616HCID 22503616, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(4-ethylpiperazin-1-yl)-3-(4-hydroxyphenyl)isoquinoline (0.30 g) obtained in Example 7 in tetrahydrofuran (15 ml) was added 60% sodium hydride (36 mg) at room temperature. After the evolution of hydrogen was ceased, bromoacetonitrile (0.11 g) was added thereto, and the resulting mixture was reacted at room temperature for 12 hr. Ethyl acetate and an aqueous solution of ammonium chloride were added to the reaction solution. The resulting organic layer was then separated, washed with water, dried and concentrated. To the resulting residue, ethanol and a 2N aqueous solution of hydrochloric acid were added, reacted at 50° C. for 30 min, followed by evaporation. The resulting residue was partitioned between ethyl acetate and water. The resulting organic layer was washed with water and brine, and dried. The solvent was removed, and the resulting residue was purified by NH-silica gel column chromatography (ethyl acetate/hexane system), to give the free compound of the title compound as a pale yellow oil. The free compound was converted into a hydrochloride in a conventional manner, to give 0.17 g of the title compound as a yellow powder.

Workup

  1. customthe resulting mixture was reacted at room temperature for 12 hr
  2. customThe resulting organic layer was then separated
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated
  6. additionTo the resulting residue, ethanol and a 2N aqueous solution of hydrochloric acid were added
  7. customreacted at 50° C. for 30 min
  8. customfollowed by evaporation
  9. customThe resulting residue was partitioned between ethyl acetate and water
  10. washThe resulting organic layer was washed with water and brine
  11. customdried
  12. customThe solvent was removed
  13. customthe resulting residue was purified by NH-silica gel column chromatography (ethyl acetate/hexane system)

Sources & evidence

ORD record
ord-5ad7d3c6563542e7ae427a5f4e281436
Source dataset
uspto-grants-2002_01
Patent number
US06340759B1

Reaction notes

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