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

HRID 566371Notes

Reaction equation

HRID 566371 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), 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 (twice). The combined organic extracts were washed with aqueous potassium carbonate, dried (magnesium sulfate) 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 (twice)
  3. washThe combined organic extracts were washed with aqueous potassium carbonate
  4. dry with materialdried (magnesium sulfate)
  5. customevaporated under reduced pressure
  6. distillationDistillation (90° C.; 0.1 mmHg)

Sources & evidence

ORD record
ord-60d279c1662d432bbdcda2f367bef024
Source dataset
uspto-grants-2001_01
Patent number
US06174894B1

Reaction notes

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