Hydrochloric Acid → HCID 66592026, compound

HRID 1091298Notes

Reaction equation

HRID 1091298 reaction equation
C([N:14]1[CH2:17][CH:16]([N:18]2[CH2:23][C@H:22]([CH3:24])[O:21][C@H:20]([CH3:25])[CH2:19]2)[CH2:15]1)(C1C=CC=CC=1)C1C=CC=CC=1.[ClH:26]>CO.[OH-].[Pd+2].[OH-]>[ClH:26].[NH:14]1[CH2:17][CH:16]([N:18]2[CH2:23][C@H:22]([CH3:24])[O:21][C@H:20]([CH3:25])[CH2:19]2)[CH2:15]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 66592200rel-(2R,6S)-4-[1-(Diphenylmethyl)-3-azetidinyl]-2,6-dimethylmorpholine

Product 1

HCID 66592026HCID 66592026, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

Cis-4-(1-benzhydryl-3-azetidinyl)-2,6-dimethylmorpholine (2.63 g, 7.82 mmol) was dissolved in methanol (40 mL), and 10% palladium hydroxide (wet) (500 mg) and a 1N-hydrochloric acid (5 mL) were added thereto. The mixture was stirred for 24 hours at room temperature under a hydrogen stream at normal pressure. The catalyst was removed by filtration, and the solvent was concentrated under reduced pressure. A 1N-hydrochloric acid (10 mL) was added to the obtained residue, and the mixture was washed with diethylether. The aqueous layer was concentrated to obtain the title compound (1.9 g, 100%) as an amorphous matter.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe solvent was concentrated under reduced pressure
  3. additionA 1N-hydrochloric acid (10 mL) was added to the obtained residue
  4. washthe mixture was washed with diethylether
  5. concentrationThe aqueous layer was concentrated

Sources & evidence

ORD record
ord-7dfecf5d2f034816a82450775b2ad451
Source dataset
uspto-grants-2012_03
Patent number
US08129366B2

Reaction notes

Loading…