Sulfuric Acid → (1-Benzyl-4-(4-cyclopropylpiperazin-1-yl)piperidin-4-yl)methanamine

HRID 45995노트

반응식

HRID 45995 반응식
[H-].[H-].[H-].[H-].[Li+].[Al+3].OS(O)(=O)=O.[CH2:12]([N:19]1[CH2:24][CH2:23][C:22]([N:27]2[CH2:32][CH2:31][N:30]([CH:33]3[CH2:35][CH2:34]3)[CH2:29][CH2:28]2)([C:25]#[N:26])[CH2:21][CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1COCC1>[CH2:12]([N:19]1[CH2:24][CH2:23][C:22]([CH2:25][NH2:26])([N:27]2[CH2:32][CH2:31][N:30]([CH:33]3[CH2:35][CH2:34]3)[CH2:29][CH2:28]2)[CH2:21][CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

참가 물질

5

반응물 3

HCID 1118Sulfuric AcidHCID 21226445Aluminium lithium hydrideHCID 579895831-Benzyl-4-(4-cyclopropylpiperazin-1-yl)piperidine-4-carbonitrile

생성물 1

HCID 57989589(1-Benzyl-4-(4-cyclopropylpiperazin-1-yl)piperidin-4-yl)methanamine수율 90%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

To a cooled (0° C.) suspension of LAH (9.24 mmol, 3.0 equiv.) in THF (2 ml/mmol) was added dropwise conc. H2SO4 (4.62 mmol, 1.5 equiv.) in THF (1 ml/mmol) and the resulting suspension was stirred at room temperature for 1.5 h. A solution of 1-benzyl-4-(4-cyclopropylpiperazin-1-yl)piperidine-4-carbonitrile (3.08 mmol, 1.0 equiv.) in THF (2 ml/mmol) was added dropwise to the reaction mixture and it was heated to 50° C. for 12 h. The mixture was quenched with sodium sulfate solution, filtered through celite and washed with ethyl acetate. The organic layer was dried over sodium sulfate and the solvent was evaporated under reduced pressure to yield the desired product. Yield: 90%

후처리

  1. temperatureTo a cooled
  2. temperaturewas heated to 50° C. for 12 h
  3. customThe mixture was quenched with sodium sulfate solution
  4. filtrationfiltered through celite
  5. washwashed with ethyl acetate
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. customthe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-d48b273bd12f467db5d8d52a808b847e
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541573B2

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