Hydrochloric Acid → 4-Morpholinopiperidine

HRID 983169Notes

Reaction equation

HRID 983169 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[CH2:10][CH2:9]1)C1C=CC=CC=1.Cl>CO.[OH-].[OH-].[Pd+2]>[NH:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 7838314-(1-Benzylpiperidin-4-yl)morpholine

Product 1

HCID 7957244-MorpholinopiperidineYield 91.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

4-(1-benzyl-piperidin-4-yl)-morpholine (1.56 g, 6.0 mmol) was hydrogenated using Pd(OH)2 (20% on carbon, 390 mg, 25 wt %), 1.7 M HCl (10.6 mL) in methanol (50 mL) at 50° C. for 10 hours. The resulted amine dihydrochloride off-white solid was subjected to free-basing using excess basic resin to give 932 mg (91%) of 4-piperidin-4-yl-morpholine as waxy crystalline solid.

Workup

  1. customat 50° C.
  2. customfor 10 hours

Sources & evidence

ORD record
ord-a2a0b1413da0425a8a994e311700cdf1
Source dataset
uspto-grants-2005_03
Patent number
US06861418B2

Reaction notes

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