Water → N-[2-[2-[(1,1-dimethylethyl)amino]ethoxy]phenyl]-1H-indol-4-carboxamide

HRID 1165218Notes

Reaction equation

HRID 1165218 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][C:12]([C:14]1[C:15]2[CH:16]=[CH:17][NH:18][C:19]=2[CH:20]=[CH:21][CH:22]=1)=[O:13].O.[OH-].[Na+].C(=O)([O-])[O-].[K+].[K+].[C:32]([NH2:36])([CH3:35])([CH3:34])[CH3:33]>C(O)C.C(OCC)(=O)C>[CH3:33][C:32]([NH:36][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][C:12]([C:14]1[C:15]2[CH:16]=[CH:17][NH:18][C:19]=2[CH:20]=[CH:21][CH:22]=1)=[O:13])([CH3:35])[CH3:34]

Participants

8

Reactant 5

HCID 962WaterHCID 6385Tert-ButylamineHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 13787419N-[2-(2-chloroethoxy)phenyl]-1H-indol-4-carboxamide

Product 1

HCID 3086996N-[2-[2-[(1,1-dimethylethyl)amino]ethoxy]phenyl]-1H-indol-4-carboxamide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

With stirring at a pressure of 2 bars, a solution of 2.3 g of the product from Step A in 40 ml of ethanol and 37.5 ml of tert-butylamine was heated at 120° C. for 24 hours. After dilution with 400 ml of water and 400 ml of ethyl acetate, the solution was alkalized with sodium hydroxide and saturated with potassium carbonate. The mixture was extracted with ethyl acetate and the crystals obtained were triturated with ether to obtain 2.3 g of N-[2-[2-[(1,1-dimethylethyl) amino]ethoxy]phenyl]-1H-indol-4-carboxamide melting at ≃148° C.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. customthe crystals obtained
  3. customwere triturated with ether

Sources & evidence

ORD record
ord-984b7fd9bb414df3a443234922e5f84e
Source dataset
uspto-grants-1990_03
Patent number
US04908367

Reaction notes

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