Hydrochloric Acid → HCID 90410566, compound

HRID 2177573Notes

Reaction equation

HRID 2177573 reaction equation
[ClH:1].Cl.[NH2:3][CH2:4][CH2:5][C:6]1[N:10]=[CH:9][NH:8][CH:7]=1.[OH-].[K+].O.[F:14][C:15]([F:19])([F:18])[CH:16]=O.Cl>O>[ClH:1].[F:14][C:15]([F:19])([F:18])[CH:16]1[C:7]2[N:8]=[CH:9][NH:10][C:6]=2[CH2:5][CH2:4][NH:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 27813662,2,2-Trifluoroacetaldehyde hydrateHCID 178478691HCID 178478691, compound

Product 1

HCID 90410566HCID 90410566, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of histamine dihydrochloride (1.0 g, 5.3 mmol) in H2O (20 mL) was cooled in an ice bath. To this suspension was added solid KOH (85%) (0.9 g, 16 mmol) followed by trifluoroacetaldehyde hydrate (0.5 g, 5.3 mmol). The reaction was allowed to warm to rt and heated to 80° C. After 6 h, the reaction was cooled to rt, acidified using 6N HCl, and concentrated. The resulting residue was dissolved in hot EtOH and filtered through Celite©. The solvent was evaporated to give the product as the HCl salt. This was purified by dissolving in minimal water and loading on silica (SiO2; MeOH(NH3):DCM) to give the title compound (0.6 g, 45%).

Workup

  1. temperaturewas cooled in an ice bath
  2. temperatureheated to 80° C
  3. temperaturethe reaction was cooled to rt
  4. concentrationconcentrated
  5. dissolutionThe resulting residue was dissolved in hot EtOH
  6. filtrationfiltered through Celite©
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-54988de457354dccbf4efa40407dd909
Source dataset
uspto-grants-2015_06
Patent number
US09066946B2

Reaction notes

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