1-Benzhydryl-3-cyclopropyl-3-fluoroazetidine hydrochloride → 3-Cyclopropyl-3-fluoroazetidine hydrochloride

HRID 490243Notes

Reaction equation

HRID 490243 reaction equation
[ClH:1].C([N:15]1[CH2:18][C:17]([CH:20]2[CH2:22][CH2:21]2)([F:19])[CH2:16]1)(C1C=CC=CC=1)C1C=CC=CC=1>[Pd].C(O)C>[ClH:1].[CH:20]1([C:17]2([F:19])[CH2:18][NH:15][CH2:16]2)[CH2:22][CH2:21]1

Participants

4

Reactant 1

HCID 665895181-Benzhydryl-3-cyclopropyl-3-fluoroazetidine hydrochloride

Product 1

HCID 665896423-Cyclopropyl-3-fluoroazetidine hydrochlorideYield 93.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Conditions

Temperature
0 °C

Procedure

To wet 10% palladium on carbon (Degussa catalyst) under nitrogen was added ethanol (100 ml). A solution of 1-Benzhydryl-3-cyclopropyl-3-fluoroazetidine hydrochloride (6.74 g, 21.23 mmol) in ethanol (50 ml) was added to the catalyst and the mixture hydrogenated at 60 psi on the Parr shaker hydrogenation apparatus for 5 hrs. The reaction was filtered through celite and concentrated to an oil. Ether (50 ml) was added and the mixture cooled to 0° C. and stirred until a precipitate formed. The suspension was filtered and the filter cake washed with ether (20 ml) and the solid dried under vacuum. This furnished the product as an off white solid (3.00 g, 93%). 1H NMR d6-DMSO δ 0.52-0.56 (2H, m), 0.59-0.64 (2H, m), 1.35-1.40 (1H, m), 3.91-4.10 (4H, m), 4.01-4.23 (4H, m), 9.50 (1H, brs), 9.63 (1H, brs).

Workup

  1. filtrationThe reaction was filtered through celite
  2. concentrationconcentrated to an oil
  3. additionEther (50 ml) was added
  4. customformed
  5. filtrationThe suspension was filtered
  6. washthe filter cake washed with ether (20 ml)
  7. customthe solid dried under vacuum

Sources & evidence

ORD record
ord-3ec0a7b2f59043d8b750fd6ae6c021c6
Source dataset
uspto-grants-2009_05
Patent number
US07528142B2

Reaction notes

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