Benzylamine → 1-Acetamido-7-benzylamino-5,6,7,8-tetrahydronaphthalene

HRID 863507노트

반응식

HRID 863507 반응식
[C:1]([NH:4][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[CH2:13][C:12](=O)[CH2:11][CH2:10]2)(=[O:3])[CH3:2].[CH2:16]([NH2:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1C=CC=CC=1.CN(C=O)C.CC1C=CC(S(O)(=O)=O)=CC=1>[C:1]([NH:4][C:5]1[C:14]2[CH2:13][CH:12]([NH:23][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:11][CH2:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

참가 물질

6

반응물 2

HCID 7504BenzylamineHCID 134241118-Acetamido-2-tetralone

생성물 1

HCID 196961461-Acetamido-7-benzylamino-5,6,7,8-tetrahydronaphthalene수율 67%

시약·촉매·용매 3

HCID 6101p-Toluenesulfonic acid촉매HCID 241Benzene용매HCID 6228Dimethylformamide용매

실험 절차

A solution of 8-acetamido-2-tetralone (15.5 g. 76 mmol), benzylamine (16.3 g, 150 mmol) and tosic acid (0.2 g) in benzene (200 mL) and DMF (50 mL) was refluxed with a Dean-Stark trap attached for 18 h. The solvent was evaporated and the residue dissolved in 1:1 methanol:THF (250 mL). After cooling in an ice bath, sodium cyanoborohydride was added and the mixture warmed to room temperature and stirred for 5 h. The mixture was basified with 12.5% NaOH and the solvent concentrated. The residue was dissolved in methylene chloride:water and filtered through a celite pad. The aqueous layer was extracted with methylene chloride, and the combined organic layers were dried over sodium sulfate, filtered and evaporated. The dark residue was purified by column chromatography (9:1 EtOAc:methanol) to give the product (15 g).

후처리

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in 1:1 methanol
  3. temperatureAfter cooling in an ice bath
  4. additionsodium cyanoborohydride was added
  5. concentrationthe solvent concentrated
  6. dissolutionThe residue was dissolved in methylene chloride
  7. filtrationwater and filtered through a celite pad
  8. extractionThe aqueous layer was extracted with methylene chloride
  9. dry with materialthe combined organic layers were dried over sodium sulfate
  10. filtrationfiltered
  11. customevaporated
  12. customThe dark residue was purified by column chromatography (9:1 EtOAc:methanol)

출처 및 근거

ORD 기록
ord-84a02ba627c548d1bd927180b386a3e7
출처 데이터셋
uspto-grants-1998_02
특허 번호
US05721234

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