Hydrogen chloride-ethyl acetate → HCID 86611680, compound

HRID 1696460Notes

Reaction equation

HRID 1696460 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][CH2:6][NH:7][C:8](=[O:13])[C:9]([F:12])([F:11])[F:10].[ClH:17].CCOC(C)=O>CCOC(C)=O>[ClH:17].[NH2:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][CH2:6][NH:7][C:8](=[O:13])[C:9]([F:10])([F:11])[F:12]

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 58723639HCID 58723639, compound

Product 1

HCID 86611680HCID 86611680, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirring solution of N-(3-aminophenethyl)-2,2,2-trifluoroacetamide (7.83 g, 33.7 mmol) in EtOAc (80 ml) at RT was added 3N HCl/EtOAc (12.4 ml, 37.1 mmol). Solids precipitated almost immediately. The resulting suspension was cooled in ice 1 h. The solids were collected by filtration, rinsed with EtOAc and dried on the filter. There was obtained pure N-(3-aminophenethyl)-2,2,2-trifluoroacetamide hydrochloride free of less polar impurities as a pale tan solid (7.94 g, 88% yield). 1H NMR 300 MHz, (DMSO-d6): δ 10.3 (brs, 3H), 9.61 (t, J=5.32 Hz, 1H), 7.43-7.39 (m, 1H), 7.25-7.23 (m, 2H), 3.42 (q, J=6.6 Hz, 2H), 2.84 (t, J=6.6 Hz, 2H).

Workup

  1. customSolids precipitated almost immediately
  2. temperatureThe resulting suspension was cooled in ice 1 h
  3. filtrationThe solids were collected by filtration
  4. washrinsed with EtOAc
  5. customdried on the filter

Sources & evidence

ORD record
ord-2593dd7af3d04e7fa2a3509de8d0de9a
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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