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

HRID 1066065Notes

Reaction equation

HRID 1066065 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 (see PREPARATION 12) (18.6 g, 60.4 mmol), 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 three days. The catalyst was then removed by filtration and the filtrate evaporated to dryness. Addition of dichloromethane (100 ml) to the residue and trituration yielded a solid which was recrystallised from methanol to give the title compound (10.2 g) as a crystalline solid.

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. customyielded a solid which
  5. customwas recrystallised from methanol

Sources & evidence

ORD record
ord-ac252939b8064dddbbb807dbbd727aa5
Source dataset
uspto-grants-2001_06
Patent number
US06242438B1

Reaction notes

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