Acetic Acid → 7-(3-Chlorobenzylamino)-1,2,3,3a,7,8,9,10b-octahydro-dicyclopenta[c,g]quinolin-4-one

HRID 1831752Notes

Reaction equation

HRID 1831752 reaction equation
[CH2:1]1[CH:13]2[CH:4]([C:5](=[O:18])[NH:6][C:7]3[CH:8]=[C:9]4[C:16](=O)[CH2:15][CH2:14][C:10]4=[CH:11][C:12]=32)[CH2:3][CH2:2]1.[Cl:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH2:23][NH2:24].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCCl.C1COCC1.C(OCC)(=O)C>[Cl:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH2:23][NH:24][CH:16]1[C:9]2[C:10](=[CH:11][C:12]3[CH:13]4[CH2:1][CH2:2][CH2:3][CH:4]4[C:5](=[O:18])[NH:6][C:7]=3[CH:8]=2)[CH2:14][CH2:15]1

Participants

8

Reactant 4

HCID 176Acetic Acid2×HCID 77802Benzenemethanamine, 3-chloro-2×HCID 5049666Sodium triacetoxyborohydride2×HCID 220525201,2,3,3a,7,8,9,10b-Octahydro-dicyclo-penta[c,g]quinoline-4,7-dione

Product 1

HCID 220525117-(3-Chlorobenzylamino)-1,2,3,3a,7,8,9,10b-octahydro-dicyclopenta[c,g]quinolin-4-oneYield 59.1%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 400 mg (1.66 mmol) of 1,2,3,3a,7,8,9,10b-octahydro-dicyclo-penta[c,g]quinoline-4,7-dione in 50 ml of 1,2-dichloroethane and 50 ml of THF is mixed with 0.22 ml (1.82 mmol) of 3-chlorobenzylamine, 526 mg (2.49 mmol) of sodium (triacetoxy)borohydride and 0.01 ml (0.17 mmol) of acetic acid. After 24 hours at room temperature, 0.44 ml (3.6 mmol) of 3-chlorobenzylamine, 1.05 g (5.0 mmol) of sodium(triacetoxy)-borohydride and 0.02 ml (0.34 mmol) of acetic acid are added to it and stirred for another 24 hours at room temperature. The reaction solution is diluted with ethyl acetate, washed with water, dried (Na2SO4) and concentrated by evaporation in a vacuum. Column chromatography on silica gel with hexane-ethyl acetate yields 360 mg of 7-(3-chlorobenzylamino)-1,2,3,3a,7,8,9,10b-octahydro-dicyclopenta[c,g]quinolin-4-one.

Workup

  1. washwashed with water
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-335beb1696f64a4c9441d99e7cc43927
Source dataset
uspto-grants-2006_06
Patent number
US07067667B2

Reaction notes

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