Benzylamine → Benzyl-(6,7,8,9-tetrahydro-5H-benzocyclohepten-7-yl)-amine

HRID 562815Notes

Reaction equation

HRID 562815 reaction equation
[CH:1]1[C:6]2[CH2:7][CH2:8][C:9](=O)[CH2:10][CH2:11][C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH2:13]([NH2:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)C.[Pd]>[CH2:13]([NH:20][CH:9]1[CH2:8][CH2:7][C:6]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[CH2:11][CH2:10]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 7504BenzylamineHCID 122344855,6,8,9-Tetrahydro-7H-benzo[7]annulen-7-one

Product 1

HCID 22499189Benzyl-(6,7,8,9-tetrahydro-5H-benzocyclohepten-7-yl)-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5,6,8,9-Tetrahydro-benzocyclohepten-7-one (3.00 g) and benzylamine (2.00 g) are dissolved in ethanol (50 mL). A catalytic amount of 10% palladium on charcoal is added and the reaction mixture is placed under an atmosphere of hydrogen. The reaction mixture is stirred at r.t. The reaction is shown to be complete by TLC after 24 hours. The catalyst is filtered off and the solvent is removed in vacuo. The product is not purified further. TLC (silica, n-hexane/ethyl acetate 1:2 Rf=0.50).

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe solvent is removed in vacuo
  3. customThe product is not purified further

Sources & evidence

ORD record
ord-49034966830a459aa7a752dc931de586
Source dataset
uspto-grants-2011_11
Patent number
US08067437B2

Reaction notes

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