Trifluoroacetic acid → HCID 66744376, compound

HRID 505085Notes

Reaction equation

HRID 505085 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[C:24]3[C:19](=[CH:20][C:21]([Cl:25])=[CH:22][CH:23]=3)[NH:18][CH:17]=2)=[O:15])[CH2:10][CH2:9]1)(C)(C)C.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[NH2:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[C:24]3[C:19](=[CH:20][C:21]([Cl:25])=[CH:22][CH:23]=3)[NH:18][CH:17]=2)=[O:15])[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 59429655HCID 59429655, compound

Product 1

HCID 66744376HCID 66744376, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 0.50 g (1.32 mmol) of [1-(6-chloro-1H-indole-3-carbonyl)-piperidin-4-yl]-carbamic acid tert-butyl ester (the preparation of which has been described in example 31) in CH2Cl2 (10 ml), were added 2 ml of TFA. The mixture was stirred 2 hours, then poured onto an aqueous solution of sat. NaHCO3 and then extracted with ethyl acetate. The combined organic phases were dried over Na2SO4 and concentrated in vacuo, to afford 0.25 g (68%) of (4-amino-piperidin-1-yl)-(6-chloro-1H-indol-3-yl)-methanone as a light brown solid.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic phases were dried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bca68f1f9d7d4be0bf10738b60d55a3b
Source dataset
uspto-grants-2010_08
Patent number
US07781436B2

Reaction notes

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