Benzylamine → HCID 18007375, compound

HRID 2299648Notes

Reaction equation

HRID 2299648 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[CH2:9][CH2:10][C:11](=O)[CH2:12][CH2:13][C:7]=2[C:6]([O:15][CH3:16])=[CH:5][CH:4]=1.[CH2:17]([NH2:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:17]([NH:24][CH:11]1[CH2:12][CH2:13][C:7]2[C:6]([O:15][CH3:16])=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:8]=2[CH2:9][CH2:10]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 521998p-Toluenesulfonic acid monohydrateHCID 11031370HCID 11031370, compound

Product 1

HCID 18007375HCID 18007375, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1,4-dimethoxy-5,6,8,9-tetrahydrobenzo-cyclohepten-7-one (670 mg) and benzylamine (0.5 ml) in toluene (60 ml) in the presence of a catalytic amount of p-toluenesulfonic acid monohydrate was refluxed for 2 hours to remove water as the toluene azeotrope, and then the mixture was evaporated in vacuo. To the residue in methanol (60 ml) was added sodium borohydride (0.5 g) under nitrogen at 5° C., and the mixture was stirred at room temperature for 12 hours. The resulting mixture was poured into ice-cold water and stirred for 30 minutes before adding ethyl acetate and brine. After separation, the organic layer was washed with brine, dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was chromatographed (hexane-ethyl acetate-methanol) over silica gel to afford N-benzyl-(1,4-dimethoxy-5,6,8,9-tetrahydrobenzcyclohepten-7-yl)amine (600 mg).

Workup

  1. customto remove water as the toluene azeotrope
  2. customthe mixture was evaporated in vacuo
  3. additionTo the residue in methanol (60 ml) was added sodium borohydride (0.5 g) under nitrogen at 5° C.
  4. additionThe resulting mixture was poured into ice-cold water
  5. stirringstirred for 30 minutes
  6. additionbefore adding ethyl acetate and brine
  7. customAfter separation
  8. washthe organic layer was washed with brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customevaporated in vacuo
  11. customThe residue was chromatographed (hexane-ethyl acetate-methanol) over silica gel

Sources & evidence

ORD record
ord-ad6c219c18cb4fe3bc3a4a945e7591f4
Source dataset
uspto-grants-2002_12
Patent number
US06495546B1

Reaction notes

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