3,4-Dimethoxyaniline → N-(3,4-Dimethoxyphenyl)-8-[2-(3,4-dimethoxyphenyl)ethyl]-8-aza-bicyclo[3.2.1]octan-3-amine

HRID 727098Notes

Reaction equation

HRID 727098 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[NH2:6].[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH2:22][CH2:23][N:24]2[CH:29]3[CH2:30][CH2:31][CH:25]2[CH2:26][C:27](=O)[CH2:28]3)[CH:17]=[CH:18][C:19]=1[O:20][CH3:21].C([BH3-])#N.[Na+]>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:6][CH:27]2[CH2:28][CH:29]3[N:24]([CH2:23][CH2:22][C:16]4[CH:17]=[CH:18][C:19]([O:20][CH3:21])=[C:14]([O:13][CH3:12])[CH:15]=4)[CH:25]([CH2:31][CH2:30]3)[CH2:26]2)[CH:7]=[CH:8][C:9]=1[O:10][CH3:11]

Participants

5

Reactant 3

HCID 227703,4-DimethoxyanilineHCID 5003444Sodium cyanoborohydrideHCID 152313198-[2-(3,4-Dimethoxyphenyl)ethyl]-8-azabicyclo[3.2.1]octane-3-one

Product 1

HCID 15200452N-(3,4-Dimethoxyphenyl)-8-[2-(3,4-dimethoxyphenyl)ethyl]-8-aza-bicyclo[3.2.1]octan-3-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 4 g (26 mmol) 3,4-dimethoxyaniline and 5 ml 14N methanolic HCl in 200 ml methanol, were added 5.7 g (20 mmol) of 8-[2-(3,4-dimethoxyphenyl)ethyl]-8-azabicyclo[3.2.1]octane-3-one (D1), followed by addition of 1 g (16 mmol) sodium cyanoborohydride. The reaction mixture was stirred overnight, slightly acidified and concentrated to dryness. The crude residue was filtered over a short column of silica gel using 95:5 methylene chloride:methanol. The expected fraction was triturated with ethyl acetate affording 4 g (47%) of the desired compound. mp.: 220° C. 1H NMR shows a mixture of two conformations of the title compound.

Workup

  1. concentrationconcentrated to dryness
  2. filtrationThe crude residue was filtered over a short column of silica gel using 95:5 methylene chloride
  3. customThe expected fraction was triturated with ethyl acetate affording 4 g (47%) of the desired compound
  4. additiona mixture of two conformations of the title compound

Sources & evidence

ORD record
ord-ea627fbbe6e24d41a023e3a07b0e6641
Source dataset
uspto-grants-1998_01
Patent number
US05712284

Reaction notes

Loading…