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

HRID 1683835

反応式

HRID 1683835 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-319bdcafd628458e80751f435c7fec4f
出典データセット
uspto-grants-1997_06
特許番号
US05639763

関連ノート

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