Hydrochloric Acid → 2-{[5-(Trifluoromethyl)pyridin-2-yl]methyl}cyclopentan-1-amine hydrochloride

HRID 1750535Notes

Reaction equation

HRID 1750535 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH:10]2[CH2:14][CH2:13][CH2:12][CH:11]2[NH:15]C(=O)OC(C)(C)C)=[N:7][CH:8]=1.[ClH:25]>O1CCOCC1>[ClH:25].[F:23][C:2]([F:1])([F:24])[C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH:10]2[CH2:14][CH2:13][CH2:12][CH:11]2[NH2:15])=[N:7][CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 118308149tert-Butyl N-(2-{[5-(trifluoromethyl)pyridin-2-yl]methyl}cyclopentyl)carbamate

Product 1

HCID 1183082132-{[5-(Trifluoromethyl)pyridin-2-yl]methyl}cyclopentan-1-amine hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of tert-butyl N-(2-{[5-(trifluoromethyl)pyridin-2-yl]methyl}cyclopentyl)carbamate (1.0 g, 2.9 mmol) in 1,4-dioxane (5 ml) at 0° C. was added drop wise HCl in 1,4-dioxane (12%, 15.0 ml). The reaction was stirred at room temperature for 1 hour, then concentrated in vacuo. To this was then added DCM (50 ml) and a solution of sodium bicarbonate (aq, 7.5%, 15 ml). The organics were dried over sodium sulfate and concentrated in vacuo. The resulting residue was purified by column chromatography (0-2% methanol/DCM) and then treated with HCl in 1,4-dioxane (12%, 5 ml), stirred for 2 hours, concentrated in vacuo, triturated with diethyl ether to afford the title compound as a single diastereomer.

Workup

  1. concentrationconcentrated in vacuo
  2. dry with materialThe organics were dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe resulting residue was purified by column chromatography (0-2% methanol/DCM)
  5. additiontreated with HCl in 1,4-dioxane (12%, 5 ml)
  6. stirringstirred for 2 hours
  7. concentrationconcentrated in vacuo
  8. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-a3c3389d980247219cffa550c542df9b
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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