Benzylamine → Benzyl-(2-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)-amine

HRID 422226Notes

Reaction equation

HRID 422226 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:12][C:11](=O)[CH2:10][CH2:9][CH2:8][C:7]=2[CH:14]=1.[CH2:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[BH3-]C#N.[Na+]>CO.C(O)(=O)C.ClCCl>[CH2:15]([NH:22][CH:11]1[CH2:10][CH2:9][CH2:8][C:7]2[CH:14]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=2[CH2:12]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 7504BenzylamineHCID 5003444Sodium cyanoborohydrideHCID 123691772-Methoxy-8,9-dihydro-5H-benzo[7]annulen-6(7H)-one

Product 1

HCID 18007141Benzyl-(2-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)-amineYield 83.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 10129899Acetic acid methanolSolvent

Procedure

Dissolve 2-Methoxy-5,7,8,9-tetrahydro-benzocyclohepten-6-one (prepared according to JCS Perkin Trans. 1, 1992, 1475-1481, 83 mg, 0.44 mmol) in 1 mL of 19:1 methanol/acetic acid as solvent, and treat the solution with benzylamine (60 uL, 65 mg, 0.60 mmol) and NaCNBH3 (80 mg, 1.27 mmol). Agitate the reaction mixture overnight, then dilute with 25 mL dichloromethane. Wash the organic layer with 25 mL 10%/aqueous potassium carbonate solution, the 25 mL brine, dry over MgSO4 and evaporate to yield 103 mg product, used in subsequent chemistry without further purification; 80% crude yield.

Workup

  1. washWash the organic layer with 25 mL 10%/aqueous potassium carbonate solution
  2. dry with materialthe 25 mL brine, dry over MgSO4
  3. customevaporate

Sources & evidence

ORD record
ord-30f86b0c7e2640cc9d1c383f85a66170
Source dataset
uspto-grants-2012_01
Patent number
US08101638B2

Reaction notes

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