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

HRID 863507ノート

反応式

HRID 863507 の反応式
[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]

参加物

6

反応物 2

HCID 7504BenzylamineHCID 134241118-Acetamido-2-tetralone

生成物 1

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

試薬・触媒・溶媒 3

HCID 6101p-Toluenesulfonic acid触媒HCID 241Benzene溶媒HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-84a02ba627c548d1bd927180b386a3e7
出典データセット
uspto-grants-1998_02
特許番号
US05721234

反応ノート

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