Trifluoroacetic acid → 2-Ethyl-6-fluoro-1-phenyl-3-piperidin-4-YL-1H-indole

HRID 2356389Notes

Reaction equation

HRID 2356389 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:22]3[C:17](=[CH:18][C:19]([F:23])=[CH:20][CH:21]=3)[N:16]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:15]=2[CH2:30][CH3:31])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:30]([C:15]1[N:16]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:17]2[C:22]([C:14]=1[CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=2)[CH3:31]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 587479994-(2-Ethyl-6-fluoro-1-phenyl-1H-indol-3-YL)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 587480002-Ethyl-6-fluoro-1-phenyl-3-piperidin-4-YL-1H-indoleYield 76.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-(2-ethyl-6-fluoro-1-phenyl-1H-indol-3-yl)-piperidine-1-carboxylic acid tert-butyl ester (0.12 g) in DCM (20 ml) at r.t., is added trifluoroacetic acid (0.5 ml). After 15 h, the mixture is concentrated in vacuo. Flash chromatography (DCM:MeOH, gradient elution) of the resulting liquid gives 70 mg pure product (57%, TFA salt) as a beige solid after trituration with diethylether.

Workup

  1. concentrationthe mixture is concentrated in vacuo
  2. washFlash chromatography (DCM:MeOH, gradient elution) of the resulting liquid

Sources & evidence

ORD record
ord-dc1cc16446f3445db528a4152ad30d23
Source dataset
uspto-grants-2010_07
Patent number
US07759365B2

Reaction notes

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