Water → 3-Chloro-N-[1-(2-chlorophenyl)-2-[1-(2,2,2-trifluoroacetyl)-piperidin-4-ylmethoxy]ethyl]-1H-indole-6-carboxamide

HRID 32427

Reaction equation

HRID 32427 reaction equation
[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([NH:13][CH:14]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:30])[CH2:15][O:16][CH2:17][CH:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)=[O:12])=[CH:8][CH:9]=2)[NH:4][CH:3]=1.C(N(CC)CC)C.C([O:40][C:41](=O)[C:42]([F:45])([F:44])[F:43])C.O>CO>[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([NH:13][CH:14]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:30])[CH2:15][O:16][CH2:17][CH:18]3[CH2:23][CH2:22][N:21]([C:41](=[O:40])[C:42]([F:45])([F:44])[F:43])[CH2:20][CH2:19]3)=[O:12])=[CH:8][CH:9]=2)[NH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 9794Ethyl trifluoroacetateHCID 693078883-chloro-N-[1-(2-chlorophenyl)-2-(piperidin-4-ylmethoxy)ethyl]-1H-indole-6-carboxamide

Product 1

HCID 866036013-Chloro-N-[1-(2-chlorophenyl)-2-[1-(2,2,2-trifluoroacetyl)-piperidin-4-ylmethoxy]ethyl]-1H-indole-6-carboxamideYield 42.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-chloro-N-[1-(2-chlorophenyl)-2-(piperidin-4-ylmethoxy)ethyl]-1H-indole-6-carboxamide (600 mg, 1.3 mmol) in 5 mL of methanol was added triethylamine (0.37 mL, 2.7 mmol) and trifluoroacetic acid ethyl ester (0.20 mL, 2.7 mmol). The reaction was allowed to stir at room temperature overnight after which time water was added and the resulting precipitate was isolated by filtration. Purification of the filtrate (SiO2: 10:2:0.5 DCM:hexane:isopropylamine) provided 297 mg (41%) of the title compound.

Workup

  1. additionwas added
  2. customthe resulting precipitate was isolated by filtration
  3. customPurification of the filtrate (SiO2: 10:2:0.5 DCM:hexane:isopropylamine)

Sources & evidence

ORD record
ord-5e244fec7d16455e9dde4969716cd94a
Source dataset
uspto-grants-2008_09
Patent number
US07427632B2

Linked notes

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