Trifluoroacetic acid → 4-(1H-pyrrolo(2,3-b)pyridin-3-yl)piperidine

HRID 1675031Notes

Reaction equation

HRID 1675031 reaction equation
C(O)(C(F)(F)F)=O.[NH:8]1[C:12]2=[N:13][CH:14]=[CH:15][CH:16]=[C:11]2[C:10]([CH:17]2[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]2)=[CH:9]1>C(Cl)Cl>[NH:20]1[CH2:19][CH2:18][CH:17]([C:10]2[C:11]3[C:12](=[N:13][CH:14]=[CH:15][CH:16]=3)[NH:8][CH:9]=2)[CH2:22][CH2:21]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 49758876tert-butyl 4-(1H-pyrrolo[2,3-b]pyridin-3-yl)piperidine-1-carboxylate

Product 1

HCID 55294774-(1H-pyrrolo(2,3-b)pyridin-3-yl)piperidineYield 88.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (5.0 mL, 3.58 mmol) was added in one portion at ambient temperature to a stirred suspension of tert-butyl 4-(1H-pyrrolo[2,3-b]pyridin-3-yl)piperidine-1-carboxylate (1.08 g, 3.58 mmol) in DCM (8 mL). The resulting solution was stirred for 30 minutes then applied to an SCX column and eluted with MeOH 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 3-(piperidin-4-yl)-1H-pyrrolo[2,3-b]pyridine (0.64 g, 88%) as a colourless solid.

Workup

  1. washeluted with MeOH
  2. concentrationconcentrated by evaporation
  3. customtriturated with ether
  4. customto give a solid which
  5. filtrationwas collected by filtration
  6. customair-dried

Sources & evidence

ORD record
ord-71808ac4b5cc47f3828d77462eebf6ca
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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