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

HRID 1683835

반응식

HRID 1683835 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-319bdcafd628458e80751f435c7fec4f
출처 데이터셋
uspto-grants-1997_06
특허 번호
US05639763

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