Hydrochloric Acid → Morpholine, 2,2-bis(methoxymethyl)-, hydrochloride (1:1)

HRID 1910401Notes

Reaction equation

HRID 1910401 reaction equation
C([N:8]1[CH2:13][CH2:12][O:11][C:10]([CH2:17][O:18][CH3:19])([CH2:14][O:15][CH3:16])[CH2:9]1)C1C=CC=CC=1.[ClH:20]>CO.[OH-].[OH-].[Pd+2]>[ClH:20].[CH3:16][O:15][CH2:14][C:10]1([CH2:17][O:18][CH3:19])[O:11][CH2:12][CH2:13][NH:8][CH2:9]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 179638462,2-Bis(methoxymethyl)-4-(phenylmethyl)morpholine

Product 1

HCID 17964181Morpholine, 2,2-bis(methoxymethyl)-, hydrochloride (1:1)

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-benzyl-2,2-bis(methoxymethyl)morpholine (6 g) and conc HCl (2.41 ml) in MeOH (60 ml) was added 20% palladium hydroxide on charcoal (1.2 g), and the whole was stirred for 2 hours at room temperature under hydrogen (2.0 atm). The catalyst was filtered off, and the filtrate was concentrated under reduced pressure to give 2,2-bis(methoxymethyl)morpholine hydrochloride (3.6 g). The obtained HCl salt was diluted with CH2Cl2 and washed with 1N—NaOH. The organic phase was concentrated under reduced pressure to give gave free form, which was used for next reaction.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-dca5a68aff94456cbc74e9d475a44c68
Source dataset
uspto-grants-2013_12
Patent number
US08603975B2

Reaction notes

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