Pentane → HCID 15670863, compound

HRID 359393Notes

Reaction equation

HRID 359393 reaction equation
CCCCC.[H-].[Na+].[F:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[CH:11][CH:10]=1.[Cl:29][CH2:30][CH2:31][CH2:32]Br>CN(C=O)C>[Cl:29][CH2:30][CH2:31][CH2:32][N:26]1[CH2:25][CH2:24][N:23]([CH:15]([C:16]2[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=2)[C:12]2[CH:11]=[CH:10][C:9]([F:8])=[CH:14][CH:13]=2)[CH2:28][CH2:27]1

Participants

6

Reactant 4

HCID 8003Pentane2×HCID 80061-Bromo-3-chloropropaneHCID 24758Sodium hydrideHCID 1529321-(Bis(4-fluorophenyl)methyl)piperazine

Product 1

HCID 15670863HCID 15670863, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Pentane (50 mL) was added to sodium hydride (0.50 g, 11 mmol of 50% suspension in mineral oil) and the mixture was stirred under nitrogen. The pentane was decanted. Anhydrous DMF (12 mL) was added and the suspension was cooled to 0° C. [Bis(4-fluorophenyl)methylpiperazine (2.9 g, 10 mmol) was added in anhydrous DMF (14 mL) at 0° C. within 10 min. The reaction mixture was allowed to warm to room temperature. After 1 h, the mixture was cooled to 0° C. and 1-chloro-3-bromopropane (5 mL, 50 mmol) in anhydrous DMF (5 mL) was added to the light green solution over a period of 10 min. The mixture was stirred under nitrogen at room temperature for 72 h. The solvents were evaporated in vacuo (1 mm Hg) at 50° C. The residue was triturated in methylene chloride and filtered through Celite. The filtrate was washed with water (2× 100 mL), dried (sodium sulfate), filtered, and the filtrate evaporated in vacuo to give crude chloropropyl compound (3.65 g). Pentane (50 mL) was added, and on the next day the pentane insoluble solid was filtered. The filtrate was evaporated in vacuo to give title compound (2.3 g, 75%) as a clear, colorless oil. 100 MHz 1H NMR (CDCl3) δ: 7.32 (m, 4H), 6.95 (m, 4H), 4.2 (s, 1H), 3.57 (m, 2H), 2.2-2.6 (m, 10H), 1.9 (m, 2H). DCI/MS (M+1) 361.

Workup

  1. customThe pentane was decanted
  2. additionAnhydrous DMF (12 mL) was added
  3. temperaturethe mixture was cooled to 0° C.
  4. stirringThe mixture was stirred under nitrogen at room temperature for 72 h
  5. customThe solvents were evaporated in vacuo (1 mm Hg) at 50° C
  6. customThe residue was triturated in methylene chloride
  7. filtrationfiltered through Celite
  8. washThe filtrate was washed with water (2× 100 mL)
  9. dry with materialdried (sodium sulfate)
  10. filtrationfiltered
  11. customthe filtrate evaporated in vacuo
  12. customto give crude chloropropyl compound (3.65 g)
  13. filtrationon the next day the pentane insoluble solid was filtered
  14. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-9e860e51a4df4f8cb0b0f1cb91d687ad
Source dataset
uspto-grants-1991_03
Patent number
US05001127

Reaction notes

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