Trifluoroacetic acid → HCID 21469421, compound

HRID 1675078Notes

Reaction equation

HRID 1675078 reaction equation
C(O)(C(F)(F)F)=O.C(OC([N:15]1[CH2:20][CH2:19][CH:18]([C:21]2[C:29]3[C:24](=[CH:25][CH:26]=[C:27]([C:30]([O:32][CH3:33])=[O:31])[CH:28]=3)[NH:23][CH:22]=2)[CH2:17][CH2:16]1)=O)(C)(C)C>C(Cl)Cl>[NH:15]1[CH2:16][CH2:17][CH:18]([C:21]2[C:29]3[C:24](=[CH:25][CH:26]=[C:27]([C:30]([O:32][CH3:33])=[O:31])[CH:28]=3)[NH:23][CH:22]=2)[CH2:19][CH2:20]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67339702HCID 67339702, compound

Product 1

HCID 21469421HCID 21469421, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (10 mL) was added in one portion at ambient temperature to a stirred solution of methyl 3-[1-(tert-butoxycarbonyl)piperidin-4-yl]-1H-indole-5-carboxylate (4.58 g, 12.78 mmol) in DCM (30 mL). The resulting solution was stirred for 30 minutes then applied to an SCX column and eluted with methanol followed by 2M ammonia in methanol. Pure fractions were combined and concentrated by evaporation then triturated with ether to give a solid which was collected by filtration and air dried to give methyl 3-(piperidin-4-yl)-1H-indole-5-carboxylate (2.69 g, 81%) as a pale yellow solid.

Workup

  1. washeluted with methanol
  2. concentrationconcentrated by evaporation
  3. customthen triturated with ether
  4. customto give a solid which
  5. filtrationwas collected by filtration and air
  6. customdried

Sources & evidence

ORD record
ord-fa1717db915d460aaee19f996ee6516d
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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