Water → HCID 18538905, compound

HRID 412909Notes

Reaction equation

HRID 412909 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[CH2:23][CH2:24][O:25][CH2:26][CH2:27]Cl.C(=O)([O-])[O-].[K+].[K+].O>C(O)CCC>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8115Bis(2-chloroethyl) etherHCID 11430Potassium CarbonateHCID 21876872tert-Butyl 4-(4-aminobenzyl)piperidine-1-carboxylate

Product 1

HCID 18538905HCID 18538905, compoundYield 69.9%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

1-tert-Butoxycarbonyl-4-(4-aminobenzyl)piperidine (1 g, 3.45 mmol) was dissolved in 1-butanol (20 mL). To the solution were added bis(2-chloroethyl) ether (490 mg, 3.45 mmol) and potassium carbonate (1 g, 7.23 mmol), and the mixture was heated for 30 hours under reflux. The reaction mixture was poured into water (50 mL), and the mixture was extracted with ethyl acetate. The extract was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and the concentrate was purified by silica gel column chromatography (hexane/ethyl acetate=3/1) to give 1-tert-butoxycarbonyl-4-(4-morpholinobenzyl)piperidine (869 mg) as a colorless oily substance. This compound (859 mg, 2.39 mmol) was dissolved in ethyl acetate (10 mL). To the solution was added 4N-hydrogen chloride in ethyl acetate (5 mL), and the mixture was stirred at room temperature for 2 hours. The solvent was distilled off under reduced pressure to give the titled compound (562 mg) as colorless powders.

Workup

  1. temperaturethe mixture was heated for 30 hours
  2. temperatureunder reflux
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customthe concentrate was purified by silica gel column chromatography (hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-7480f6d2e71442a69623d3d5866ba8ff
Source dataset
uspto-grants-2003_05
Patent number
US06562978B1

Reaction notes

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