Ethyl 4-piperidinecarboxylate → ethyl N-[4-(2-propen-1-yloxy)phenylmethyl]piperidin-4-ylcarboxylate

HRID 1683835Notes

Reaction equation

HRID 1683835 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]1.[CH2:12]([O:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=1)[CH:13]=[CH2:14]>C(O)C.O>[CH2:12]([O:15][C:16]1[CH:17]=[CH:18][C:19]([CH2:20][N:1]2[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]2)=[CH:22][CH:23]=1)[CH:13]=[CH2:14]

Participants

5

Reactant 2

HCID 70770Ethyl 4-piperidinecarboxylateHCID 959424-(Allyloxy)benzaldehyde

Product 1

HCID 19040934ethyl N-[4-(2-propen-1-yloxy)phenylmethyl]piperidin-4-ylcarboxylateYield 98.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The reaction conditions taught by A. E. Moormann, Syn. Comm., 23(6), 789-795 (1993) were used in the following preparation. To a stirred solution of 4.8 grams (0.030 mole) of ethyl piperidin-4-ylcarboxylate and 4.9 grams (0.030 mole) of 4-(2-propen-1-yloxy)benzaldehyde in 50 mL of ethanol was added 3.8 mL (0.030 mole) of borane-pyridine complex. Upon completion of addition, the reaction mixture was stirred at ambient temperature for about 18 hours. The reaction mixture was then taken up in water and extracted with methylene chloride. The organic layer was washed with water and dried with magnesium sulfate. The mixture was filtered and the filtrate concentrated under reduced pressure, yielding 9.0 grams of ethyl N-[4-(2-propen-1-yloxy)phenylmethyl]piperidin-4-ylcarboxylate. The NMR spectrum was consistent with the proposed structure.

Workup

  1. customThe reaction conditions
  2. custom, 23(6), 789-795 (1993) were used in the following preparation
  3. additionUpon completion of addition
  4. extractionextracted with methylene chloride
  5. washThe organic layer was washed with water
  6. dry with materialdried with magnesium sulfate
  7. filtrationThe mixture was filtered
  8. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-319bdcafd628458e80751f435c7fec4f
Source dataset
uspto-grants-1997_06
Patent number
US05639763

Reaction notes

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