Hydrochloric Acid → 4-(Azetidin-3-yl)morpholine dihydrochloride

HRID 1384797Notes

Reaction equation

HRID 1384797 reaction equation
C1(C(C2C=CC=CC=2)[N:8]2[CH2:11][CH:10]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[CH2:9]2)C=CC=CC=1.[ClH:24]>[OH-].[Pd+2].[OH-].C(O)C>[ClH:24].[ClH:24].[O:15]1[CH2:16][CH2:17][N:12]([CH:10]2[CH2:11][NH:8][CH2:9]2)[CH2:13][CH2:14]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 211837864-[1-(Diphenylmethyl)azetidin-3-yl]morpholine

Product 1

HCID 220613264-(Azetidin-3-yl)morpholine dihydrochloride

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-diphenylmethyl-3-morpholinoazetidine (prepared in an analogous manner to the compound of preparation 22 above) (18.6 g), palladium hydroxide (2 g), ethanol (200 ml) and 1N aqueous hydrochloric acid solution (52 ml) was stirred under an atmosphere of hydrogen at 345 kPa (50 p.s.i.) for 3 days. The catalyst was then removed by filtration and the filtrate evaporated to dryness. Addition of dichloromethane (100 ml) to the residue and trituration gave a solid which was recrystallised from methanol to give the title compound (10.2 g).

Workup

  1. customThe catalyst was then removed by filtration
  2. customthe filtrate evaporated to dryness
  3. additionAddition of dichloromethane (100 ml) to the residue and trituration
  4. customgave a solid which
  5. customwas recrystallised from methanol

Sources & evidence

ORD record
ord-7ad0e197b7a94a1fa2a8b5c8fcdc2e0d
Source dataset
uspto-grants-2001_07
Patent number
US06262046B1

Reaction notes

Loading…