Trifluoroacetic acid → (1-(2-Aminoethyl)-1H-indol-5-yl)(4-(4-chlorophenoxy)piperidin-1-yl)methanone

HRID 2170863Notes

Reaction equation

HRID 2170863 reaction equation
[Cl:1][C:2]1[CH:35]=[CH:34][C:5]([O:6][CH:7]2[CH2:12][CH2:11][N:10]([C:13]([C:15]3[CH:16]=[C:17]4[C:21](=[CH:22][CH:23]=3)[N:20]([CH2:24][CH2:25][NH:26]C(=O)OC(C)(C)C)[CH:19]=[CH:18]4)=[O:14])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[NH2:26][CH2:25][CH2:24][N:20]1[C:21]2[C:17](=[CH:16][C:15]([C:13]([N:10]3[CH2:9][CH2:8][CH:7]([O:6][C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[CH:35][CH:34]=4)[CH2:12][CH2:11]3)=[O:14])=[CH:23][CH:22]=2)[CH:18]=[CH:19]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86670543tert-Butyl (2-(5-(4-(4-chlorophenoxy)piperidine-1-carbonyl)-1H-indol-1-yl)ethyl)carbamate

Product 1

HCID 67168198(1-(2-Aminoethyl)-1H-indol-5-yl)(4-(4-chlorophenoxy)piperidin-1-yl)methanoneYield 90.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl (2-(5-(4-(4-chlorophenoxy)piperidine-1-carbonyl)-1H-indol-1-yl)ethyl)carbamate (112 mg, 0.23 mmol, Step-1), trifluoroacetic acid (1.5 mL), and dichloromethane (1.5 mL) was stirred at room temperature for 1 hour. After concentration in vacuo, the residue was purified by a strong cation exchange cartridge (BondElute(registered trademark) SCX) to give 83 mg (83% yield) of the title compound as yellow oil. 13 mg of this material was further purified by preparative LC-MS to give 6.6 mg (51% yield) of the title compound.

Workup

  1. concentrationAfter concentration in vacuo
  2. customthe residue was purified by a strong cation exchange cartridge (BondElute(registered trademark) SCX)

Sources & evidence

ORD record
ord-f561978c1a694e96bb0f52ae68eecc85
Source dataset
uspto-grants-2015_06
Patent number
US09051296B2

Reaction notes

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