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

HRID 863507Notes

Reaction equation

HRID 863507 reaction equation
[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]

Participants

6

Reactant 2

HCID 7504BenzylamineHCID 134241118-Acetamido-2-tetralone

Product 1

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

Reagents, catalysts & solvents 3

HCID 6101p-Toluenesulfonic acidCatalystHCID 241BenzeneSolventHCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-84a02ba627c548d1bd927180b386a3e7
Source dataset
uspto-grants-1998_02
Patent number
US05721234

Reaction notes

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