Potassium Carbonate → 4-(1-Benzylpiperidin-4-yl)morpholine

HRID 983168Notes

Reaction equation

HRID 983168 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.C([O-])([O-])=O.[K+].[K+].Br[CH2:22][CH2:23][O:24][CH2:25][CH2:26]Br>CN(C=O)C>[CH2:8]([N:5]1[CH2:6][CH2:7][CH:2]([N:1]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[CH2:3][CH2:4]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21521Bis(2-bromoethyl) etherHCID 4158521-Benzyl-4-piperidylamine

Product 1

HCID 7838314-(1-Benzylpiperidin-4-yl)morpholineYield 87.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred mixture of 4-amino-1-benzylpiperidine (1.53 mL, 7.5 mmol), K2CO3 (2.28 g, 16.5 mmol) and DMF (15 mL) heated at 50° C. was added dropwise over 60 min bis(2-bromoethyl) ether (0.96 mL, 7.65 mmol). After stirring for 6 hours at 80° C., the solvent was removed by blowing with a stream of nitrogen over 2 hours. The residue was purified on a silica gel column to give 1.7 g (87%) of 4-(1-benzyl-piperidin-4-yl)morpholine as a waxy solid.

Workup

  1. customthe solvent was removed
  2. waitby blowing with a stream of nitrogen over 2 hours
  3. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-08bb54aa0ab244ff90317c31f9d4c5e8
Source dataset
uspto-grants-2005_03
Patent number
US06861418B2

Reaction notes

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