Pentane → HCID 15670863, compound

HRID 1493551Notes

Reaction equation

HRID 1493551 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 (10 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) in anhydrous DMF (14 mL) was added 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 to the light green solution 1-chloro-3-bromopropane (5 mL, 50 mmol) in anhydrous DMF (5 mL) was added 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 was evaporated in vacuo to give crude chloro-propyl compound (3.65 g). Pentane (50 mL) was added, and on the next day the pentane insoluble solid was removed by filtration. The filtrate was evaporated in vacuo to give the 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. additionwas added at 0° C. within 10 min
  4. additionwas added over a period of 10 min
  5. stirringThe mixture was stirred under nitrogen at room temperature for 72 h
  6. customThe solvents were evaporated in vacuo (1 mm Hg) at 50° C
  7. customThe residue was triturated in methylene chloride
  8. filtrationfiltered through celite
  9. washThe filtrate was washed with water (2×100 mL)
  10. dry with materialdried (sodium sulfate)
  11. filtrationfiltered
  12. customthe filtrate was evaporated in vacuo
  13. customto give crude chloro-propyl compound (3.65 g)
  14. customon the next day the pentane insoluble solid was removed by filtration
  15. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-c42b7db841bc4544a318cff4ac0f7cad
Source dataset
uspto-grants-1991_06
Patent number
US05021574

Reaction notes

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