2,2,2-Trifluoroethylamine hydrochloride → HCID 18519913, compound

HRID 1936728Notes

Reaction equation

HRID 1936728 reaction equation
CO[CH:3]1[CH2:7][CH2:6][CH:5](OC)[O:4]1.Cl.[F:11][C:12]([F:16])([F:15])[CH2:13][NH2:14].[CH2:17]([C:24](O)=O)[C:18](CC(O)=O)=O.C([O-])(=O)C.[Na+]>Cl.O.C(=O)([O-])[O-].[K+].[K+]>[F:11][C:12]([F:16])([F:15])[CH2:13][N:14]1[CH:6]2[CH2:5][CH2:24][CH:17]1[CH2:18][C:3](=[O:4])[CH2:7]2

Participants

8

Reactant 4

HCID 97722,2,2-Trifluoroethylamine hydrochlorideHCID 68328Acetonedicarboxylic acidHCID 790982,5-DimethoxytetrahydrofuranHCID 517045Sodium Acetate

Product 1

HCID 18519913HCID 18519913, compoundYield 33.7%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 962WaterSolvent2×HCID 11430Potassium CarbonateSolvent

Procedure

A few drops of dilute hydrochloric acid were added to a solution of 2,5-dimethoxytetrahydrofuran (16.5 g) in water (70 ml). After stirring at room temperature for 30 minutes 2,2,2-trifluoroethylamine hydrochloride (16.9 g), 1,3-acetonedicarboxylic acid (18.3 g) and sodium acetate (10.0 g) were added and the mixture stirred at room temperature for 2 days. The mixture was diluted to 500 ml with water, saturated with potassium carbonate and extracted with ethyl acetate (×2). The combined organic extracts were washed with aqueous potassium carbonate, dried (MgSO4) and evaporated under reduced pressure. Distillation (90° C.; 0.1 mmHg) gave 8-(2,2,2-trifluoroethyl)-8-azabicyclo[3.2.1]octan-3-one (8.7 g).

Workup

  1. additionwere added
  2. extractionextracted with ethyl acetate (×2)
  3. washThe combined organic extracts were washed with aqueous potassium carbonate
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure
  6. distillationDistillation (90° C.; 0.1 mmHg)

Sources & evidence

ORD record
ord-661d6ecaa1414c4aa2091257427a6c0c
Source dataset
uspto-grants-2002_05
Patent number
US06391883B1

Reaction notes

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