Benzylamine → HCID 18007141, compound

HRID 747976Notes

Reaction equation

HRID 747976 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 18007141HCID 18007141, compoundYield 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-3568d788e3844f408d6af9ef6cfa6705
Source dataset
uspto-grants-2008_07
Patent number
US07399774B2

Reaction notes

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