1-Acetylnaphthalene → HCID 69200119, compound

HRID 1393133Notes

Reaction equation

HRID 1393133 reaction equation
[CH3:1][C:2]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1)=O.N[CH2:15][CH2:16][CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22].[BH3-]C#[N:28].[Na+]>C(#N)C.[Cl-].[Cl-].[Zn+2]>[C:21]([O:20][C:19](=[O:25])[NH:18][CH2:17][CH:16]([NH:28][CH:2]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1)[CH3:1])[CH3:15])([CH3:22])([CH3:23])[CH3:24]

Participants

6

Reactant 3

HCID 136631-AcetylnaphthaleneHCID 2735700tert-Butyl (3-aminopropyl)carbamateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 69200119HCID 69200119, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1-acetonaphthone (152 μl, 1 mmol) in acetonitrile (2 ml) was added tert-butyl N-(3-aminopropyl)-carbamate (209 μl, 1.2 mmol), NaBH3CN (126 mg, 2 mmol) and anhydrous ZnCl2 (136 mg, 1 mmol). The reaction was heated for 70 hours at 80° C. in a screw cap vial with magnetic stirring. The precipitate was filtered off and the solution was evaporated. The residue was dissolved in 3 ml 0.1N HCl and extracted with methylenchloride (1×5 ml). The organic layer was dried (Na2SO4) and evaporated. The crude product was purified by silica gel flash chromatography using 1. CHCl2/MeOH (10/0.1) and 2. CH2Cl2/MeOH (10/1), as an eluent, to give an oily product 70%. The structure characterization of the products was made with 1HNMR; 13CNMR; MS (m/z): 329 (MH+).

Workup

  1. customcap vial with magnetic stirring
  2. filtrationThe precipitate was filtered off
  3. customthe solution was evaporated
  4. dissolutionThe residue was dissolved in 3 ml 0.1N HCl
  5. extractionextracted with methylenchloride (1×5 ml)
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. customevaporated
  8. customThe crude product was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-751b85e8ee504caa8ead121bd9e4ec21
Source dataset
uspto-grants-2008_03
Patent number
US07345048B2

Reaction notes

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