Water → HCID 29004952, compound

HRID 1666885Notes

Reaction equation

HRID 1666885 reaction equation
C(O)(=O)C(O)=O.[F:7][C:8]([F:22])([CH:19]([F:21])[F:20])[CH2:9][O:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH2:14][NH2:15].ClCCl.[OH-].[Na+].O>CO>[F:7][C:8]([F:22])([CH:19]([F:20])[F:21])[CH2:9][O:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH2:14][NH2:15]

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 131726180HCID 131726180, compound

Product 1

HCID 29004952HCID 29004952, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Combine N-2-(5-chloro-1H-indol-3-yl)ethyl)-(3-(2,2,3,3-tetrafluoropropoxy)benzylamine oxalic acid salt and dichloromethane (700 mL) and add NaOH 1N (150 mL), water (450 mL) and MeOH (190 mL). Stir the mixture for 1 h at room temperature. Separate the layers. Add water (200 mL) to the aqueous phase and extract with dichloromethane, combine the organic layers, dry over MgSO4, filter, and evaporate under vacuum to afford 19.4 g of N-2-(5-chloro-1H-indol-3-yl)ethyl)-3-(2,2,3,3-tetrafluoropropoxy)benzylamine.

Workup

  1. customSeparate the layers
  2. extractionAdd water (200 mL) to the aqueous phase and extract with dichloromethane
  3. dry with materialdry over MgSO4
  4. filtrationfilter
  5. customevaporate under vacuum

Sources & evidence

ORD record
ord-f8c7c6502a274e90b0f9e23064c9141b
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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