Piperidine → HCID 54391668, compound

HRID 988338Notes

Reaction equation

HRID 988338 reaction equation
Br[CH2:2][CH2:3][CH2:4][O:5][N:6]=[C:7]([O:9][CH2:10][CH3:11])[CH3:8].[NH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.C1CCN2C(=NCCC2)CC1.[Cl-].[NH4+]>ClCCl>[N:12]1([CH2:2][CH2:3][CH2:4][O:5][N:6]=[C:7]([O:9][CH2:10][CH3:11])[CH3:8])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 8082PiperidineHCID 25517Ammonium ChlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 53646761ethyl N-(3-bromopropoxy)acetoimidate

Product 1

HCID 54391668HCID 54391668, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 500 mg (2.23 mmol) portion of ethyl N-(3-bromopropoxy)acetoimidate was dissolved in 6 ml of dichloromethane, and the solution was mixed with 0.22 ml (2.23 mmol) of piperidine and 0.33 ml (2.23 mmol) of 1,8-diazabicyclo[5.4,0]-7-undecene and stirred at room temperature for 36 hours. The reaction solution was mixed with a saturated ammonium chloride aqueous solution and extracted with chloroform. The chloroform layer was washed with saturated brine and dried with anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel chromatography (chloroform/methanol=10/1) to obtain 166 mg (yield, 32%) of ethyl N-(3-piperidinopropoxy)acetoimidate.

Workup

  1. extractionextracted with chloroform
  2. washThe chloroform layer was washed with saturated brine
  3. dry with materialdried with anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe resulting residue was purified by silica gel chromatography (chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-c18b9bed01bc402b8e0ba36ac65c23a0
Source dataset
uspto-grants-2003_10
Patent number
US06635662B2

Reaction notes

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