Toluene → HCID 11645176, compound

HRID 2105173Notes

Reaction equation

HRID 2105173 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C[Al](C)C.C1(C)C=CC=CC=1.[CH3:18][O:19][C:20]([C:22]1[N:23]=[N:24][C:25]([C:32](OC)=[O:33])=[CH:26][C:27]=1[CH2:28][CH:29]([CH3:31])[CH3:30])=[O:21]>C(Cl)Cl>[CH3:18][O:19][C:20]([C:22]1[N:23]=[N:24][C:25]([C:32]([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:33])=[CH:26][C:27]=1[CH2:28][CH:29]([CH3:31])[CH3:30])=[O:21]

Participants

6

Reactant 4

HCID 1140TolueneHCID 8082PiperidineHCID 16682925TrimethylaluminumHCID 57423229HCID 57423229, compound

Product 1

HCID 11645176HCID 11645176, compoundYield 54.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

An oven dried, nitrogen cooled two-necked 25 mL round bottom flask was charged with a solution of 78 μL piperidine (0.793 mmol, 68 mg) in 4.0 mL anhydrous DCM. Trimethyl aluminum was added slowly (2.0M/toluene, 436 μL, 0.872 mmol). The resulting mixture was stirred for twenty minutes at room temperature. To this solution was added 200 mg of the diester 3 (0.793 mmol) dissolved in 2.0 mL anhydrous DCM. The flask was sealed and heated to 41° C. for 15 hours. The reaction was allowed to cool to room temperature and quenched with slow addition of 1M HCl. The product was extracted three times with DCM, the organic fractions collected, washed with brine, dried over magnesium sulfate and evaporated to give a brownish/yellow oil. The crude mixture was applied to a column of silica gel and eluted with a 2:1 hexane-ethyl acetate solution (Rf=0.16) to give 132 mg of product (54% yield) as a yellow oil. MS: (ESI-TOF) MH+ expected: 306.1812, found: 306.1807.

Workup

  1. customAn oven dried
  2. customThe flask was sealed
  3. temperatureheated to 41° C. for 15 hours
  4. temperatureto cool to room temperature
  5. customquenched with slow addition of 1M HCl
  6. extractionThe product was extracted three times with DCM
  7. customthe organic fractions collected
  8. washwashed with brine
  9. dry with materialdried over magnesium sulfate
  10. customevaporated
  11. customto give a brownish/yellow oil
  12. washeluted with a 2:1 hexane-ethyl acetate solution (Rf=0.16)

Sources & evidence

ORD record
ord-1cd26d81867443f783409d281a46e943
Source dataset
uspto-grants-2009_08
Patent number
US07579350B2

Reaction notes

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