Benzylamine → HCID 18007266, compound

HRID 2299642Notes

Reaction equation

HRID 2299642 reaction equation
[CH3:1][O:2][C:3]1[C:13]2[CH2:12][C:11](=O)[CH2:10][CH2:9][CH2:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.[CH2:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:15]([NH:22][CH:11]1[CH2:10][CH2:9][CH2:8][C:7]2[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:13]=2[CH2:12]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 521998p-Toluenesulfonic acid monohydrateHCID 18007432HCID 18007432, compound

Product 1

HCID 18007266HCID 18007266, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-one (500 mg) and benzylamine (0.29 ml) in the presence of catalytic amounts of p-toluenesulfonic acid monohydrate in toluene (5 ml) was refluxed for 2 hours to remove water as the toluene azeotrope, and then the mixture was evaporated in vacuo. To the solution of the residue in methanol (5 ml) was added sodium borohydride (99 mg) under nitrogen at 5° C., and the mixture was stirred at room temperature for 12 hours. After the resulting mixture was evaporated in vacuo, the residue was dissolved into ice-cold water and ethyl acetate. After separation, the organic layer was washed successively with water and brine, dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=5:1 to 1:1) to give N-benzyl-(4-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amine (660 mg).

Workup

  1. customto remove water as the toluene azeotrope
  2. customthe mixture was evaporated in vacuo
  3. additionTo the solution of the residue in methanol (5 ml) was added sodium borohydride (99 mg) under nitrogen at 5° C.
  4. customAfter the resulting mixture was evaporated in vacuo
  5. dissolutionthe residue was dissolved into ice-cold water and ethyl acetate
  6. customAfter separation
  7. washthe organic layer was washed successively with water and brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customevaporated in vacuo
  10. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=5:1 to 1:1)

Sources & evidence

ORD record
ord-2cb7e67b59bb4702ae82840ce9f570e7
Source dataset
uspto-grants-2002_12
Patent number
US06495546B1

Reaction notes

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