Acetic Acid → HCID 67491863, compound

HRID 1921145Notes

Reaction equation

HRID 1921145 reaction equation
[CH3:1][CH:2]1[C:7](=O)[CH:6]2[CH2:9][CH2:10][N:3]1[CH2:4][CH2:5]2.[CH3:11][O:12][C:13]1[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:14]=1[CH2:15][NH2:16].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCCl>[CH3:11][O:12][C:13]1[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:14]=1[CH2:15][NH:16][CH:7]1[CH:6]2[CH2:9][CH2:10][N:3]([CH2:4][CH2:5]2)[CH:2]1[CH3:1]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5972502,4-DimethoxybenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 123816982-Methyl-1-azabicyclo(2.2.2)octan-3-one

Product 1

HCID 67491863HCID 67491863, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

2-Methyl-1-aza-bicyclo[2.2.2]octan-3-one (500 mg, 3.59 mmol) and 2,4-dimethoxybenzyl amine (1.2 g, 7.18 mmol) were dissolved in anhydrous 1,2-dichloroethane (10 ml). Sodium triacetoxyborohydride (1.1 g, 5.0 mmol) followed by glacial acetic acid (0.21 ml, 3.59 mmol) and the resultant foamy suspension was stirred at ambient temperature for 12 hours. The reaction was quenched by the addition of 1M NaOH, and the layers were separated. The aqueous phase was extracted further with ethyl acetate. The organic portions were combined, dried (Na2SO4), filtered and concentrated in vacuo. The crude reaction mixture was purified by chromatography [eluent gradient: 10-30% MeOH/Et3N (9:1) in EtOAc) to give pure (2,4-dimethoxy-benzyl)-(2-methyl-1-aza-bicyclo[2.2.2]oct-3-yl)-amine.

Workup

  1. customThe reaction was quenched by the addition of 1M NaOH
  2. customthe layers were separated
  3. extractionThe aqueous phase was extracted further with ethyl acetate
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude reaction mixture
  8. customwas purified by chromatography [eluent gradient

Sources & evidence

ORD record
ord-86ebb229af4e42838deab0108e307fb2
Source dataset
uspto-grants-2012_05
Patent number
US08173667B2

Reaction notes

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