Benzylamine → HCID 18007303, 화합물

HRID 274043노트

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HRID 274043 반응식
[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]2[CH2:7][CH2:8][CH2:9][C:10](=O)[CH2:11][C:5]=2[CH:4]=1.[CH2:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([BH3-])#N.[Na+].[OH-].[Na+]>O.C([BH3-])#N.[Na+].C(O)(=O)C>[CH2:15]([NH:22][CH:10]1[CH2:9][CH2:8][CH2:7][C:6]2[CH:13]=[CH:14][C:3]([O:2][CH3:1])=[CH:4][C:5]=2[CH2:11]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

참가 물질

8

반응물 4

HCID 7504Benzylamine2회HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 105595743-Methoxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-6-one

생성물 1

HCID 18007303HCID 18007303, 화합물

시약·촉매·용매 3

HCID 5003444Sodium cyanoborohydride촉매HCID 176Acetic Acid용매HCID 962Water용매

실험 절차

To a mixture of 3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-one (3.6 g), benzylamine (2.5 ml), and acetic acid (27 ml) in water bath was added portionwise sodium cyanoborohydride (0.49 g), and the mixture was stirred at ambient temperature for 5 hours. Additional benzylamine (2.5 ml) and sodium cyanoborohydride (0.10 g) were added to the mixture, and stirring was continued for an additional 2 hours. The reaction mixture was made alkaline (pH>8) with 10% sodium hydroxide (150 ml), and extracted once with ethyl acetate. The extract was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (gradient elution; n-hexane-ethyl acetate; 3:1 to 2:1 to 1:1) to give N-benzyl-3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-amine (4.8 g) as an oil.

후처리

  1. stirringstirring
  2. waitwas continued for an additional 2 hours
  3. extractionextracted once with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography on silica gel (gradient elution; n-hexane-ethyl acetate; 3:1 to 2:1 to 1:1)

출처 및 근거

ORD 기록
ord-0906f7099905489692a4cce3391e5e4a
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05387710

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