Pyridine → HCID 18348179, compound

HRID 2267964Notes

Reaction equation

HRID 2267964 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH2:11][C:12](Cl)=[O:13])=[CH:8][CH:7]=[CH:6][CH:5]=2.[F:15][C:16]1[CH:21]=[CH:20][C:19]([CH:22]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)=[CH:18][CH:17]=1.N1C=CC=CC=1.C(=O)(O)[O-].[Na+]>O1CCCC1.C(OCC)(=O)C>[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH2:11][C:12]([N:26]1[CH2:25][CH2:24][N:23]([CH:22]([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)[C:19]3[CH:18]=[CH:17][C:16]([F:15])=[CH:21][CH:20]=3)[CH2:28][CH2:27]1)=[O:13])=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

7

Reactant 4

HCID 1049PyridineHCID 1529321-(Bis(4-fluorophenyl)methyl)piperazineHCID 516892Sodium BicarbonateHCID 18348175HCID 18348175, compound

Product 1

HCID 18348179HCID 18348179, compoundYield 53.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Under a nitrogen atmosphere a 15 mL solution of 2-methylindol-3-ylacetyl chloride (0.013 mole) in tetrahydrofuran was added to a stirred solution of 3.9 grams (0.014 mole) of N-[bis(4-fluorophenyl)methyl]piperazine and 1.1 mL (0.013 mole) of pyridine in 50 mL of dried tetrahydrofuran. Upon completion of the addition the reaction mixture was stirred at ambient temperature for about 18 hours, after which the reaction mixture was poured into a mixture of 200 mL of ethyl acetate and 100 mL of aqueous saturated sodium bicarbonate solution. The organic layer was separated and washed with one portion of a saturated sodium chloride solution, dried with sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure to a solid, which was taken up in hexane. This solution was concentrated under reduced pressure, yielding 3.2 grams of N-(2-methylindol-3-ylacetyl)-N′-[bis(4-fluorophenyl)methyl]piperazine, mp 93-103° C. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of the addition the reaction mixture
  2. customThe organic layer was separated
  3. washwashed with one portion of a saturated sodium chloride solution
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure to a solid, which
  7. concentrationThis solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-46f8eed382604ce0ac04a0da02c41454
Source dataset
uspto-grants-2001_12
Patent number
USH0002007H1

Reaction notes

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