Hydrochloric Acid → Methyl alpha-[3-(trifluoromethyl)benzylamino]-1-benzylindole-3-acetate

HRID 5607Notes

Reaction equation

HRID 5607 reaction equation
[C:1](Cl)(=O)C.Cl.[F:6][C:7]([F:37])([F:36])[C:8]1[CH:9]=[C:10]([CH:33]=[CH:34][CH:35]=1)[CH2:11][NH:12][CH:13]([C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:18]=1)[C:14]([OH:16])=[O:15].C([O-])(O)=O.[Na+]>CO>[F:37][C:7]([F:6])([F:36])[C:8]1[CH:9]=[C:10]([CH:33]=[CH:34][CH:35]=1)[CH2:11][NH:12][CH:13]([C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:18]=1)[C:14]([O:16][CH3:1])=[O:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 516892Sodium Bicarbonate2×HCID 53973377HCID 53973377, compound

Product 1

HCID 54131001Methyl alpha-[3-(trifluoromethyl)benzylamino]-1-benzylindole-3-acetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a magnetically stirred solution of 100 ml of methanol cooled in an ice-acetone bath at ca. -15° C., was treated dropwise with acetyl chloride (27.3 g, 350 mmol, 35 eq) over a six-minute period as a convenient way to generate HCl in situ. The solution was stirred at ambient temperature for 45 minutes, then solid α-[3-(trifluoromethyl)benzylamino]-1-benzylindole-3-acetic acid was added which formed a dark rose colored solution. After stirring for 22 hours the reaction mixture was poured into 100 mL of saturated NaHCO3 solution containing 100 mL of crushed ice, basified with additional solid NaHCO3 powder until the rose color dissipated and extracted twice with ether. The combined organic extracts were washed with saturated NaHCO3 (1×75 mL), saturated brine (1×100 mL), dried with anhydrous NaSO4 and concentrated in vacuo. Flash chromatography with 100 g of silica gel using ethyl acetate-hexane (1:2) afforded 4.07 g of the title compound as a golden oil.

Workup

  1. customformed a dark
  2. stirringAfter stirring for 22 hours the reaction mixture
  3. extractionextracted twice with ether
  4. washThe combined organic extracts were washed with saturated NaHCO3 (1×75 mL), saturated brine (1×100 mL)
  5. dry with materialdried with anhydrous NaSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f5076b126f9c44638f9cffe98c7e0417
Source dataset
uspto-grants-1993_09
Patent number
US05245046

Reaction notes

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