Hydrochloric Acid → HCID 55300015, compound

HRID 2426799Notes

Reaction equation

HRID 2426799 reaction equation
C([N:8]([CH2:13][CH:14]1[CH2:16][CH:15]1[CH3:17])[CH2:9][CH:10]([F:12])[F:11])C1C=CC=CC=1.Cl>O1CCOCC1.C(O)C.[OH-].[Pd+2].[OH-]>[F:11][CH:10]([F:12])[CH2:9][NH:8][CH2:13][CH:14]1[CH2:16][CH:15]1[CH3:17]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 86617873HCID 86617873, compound

Product 1

HCID 55300015HCID 55300015, compound

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of N-benzyl-2,2-difluoro-N-[(2-methylcyclopropyl)methyl]ethanamine (1.25 g, 5.2 mmol) and hydrochloric acid (5.7 mmol, 1.44 mL of a 4M solution in dioxane) in ethanol (50 mL) was degassed with nitrogen and treated with palladium hydroxide (125 mg). The reaction was placed under a hydrogen atmosphere and stirred vigorously for 1 hour. The reaction was filtered through celite, washed with methanol and concentrated in vacuo to give (2,2-difluoroethyl)[(2-methylcyclopropyl)methyl]amine as a pale yellow oil: 1H NMR (400 MHz, CD3OD) δ 6.35 (tt, 48, 3 Hz, 1H), 3.56 (td, J=15.6, 3.1 Hz, 2H), 3.03 (m, 2H), 1.11 (d, J=5.9 Hz, 3H), 0.83 (m, 2H), 0.60 (m, 1H), 0.50 (m, 1H).

Workup

  1. filtrationThe reaction was filtered through celite
  2. washwashed with methanol
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cdb0f8b765464db6835d502b7f92bbb4
Source dataset
uspto-grants-2011_06
Patent number
US07968571B2

Reaction notes

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