Water → Donepezil

HRID 1881740Notes

Reaction equation

HRID 1881740 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4](S(O)(=O)=O)=[CH:3][CH:2]=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][C:22]=1[O:23][CH3:24])[C:19](=[O:25])[CH:18]([CH2:26][CH:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1)[CH2:17]2.C(Br)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH3:12][O:13][C:14]1[CH:15]=[C:16]2[CH2:17][CH:18]([CH2:26][CH:27]3[CH2:32][CH2:31][N:30]([CH2:11][C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[CH2:29][CH2:28]3)[C:19](=[O:25])[C:20]2=[CH:21][C:22]=1[O:23][CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 86611641HCID 86611641, compound

Product 1

HCID 3152DonepezilYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.18 g of 2,3-dihydro-5,6-dimethoxy-2-((piperidin-4-yl)methyl)inden-1-one p-toluenesulfonic acid salt were dissolved in 10 mL of dry N,N′-dimethylformamide. 0.073 g of benzyl bromide and 0.3 g of potassium carbonate were added thereto. The resulted mixture was stirred until the reaction completed. Then 60 mL of water were added and the solution was extracted with 4×30 mL of ethyl acetate. The extracts were combined, washed with 15 mL of Na2CO3 solution and with 15 mL NaCl solution, and dried over anhydrous MgSO4. Drying agent was then filtered off. The solvent was removed in vacuo yielding 0.141 g of product, 96% yield. 1H NMR (CDCl3), 7.15-7.35 (m, 5H), 7.09 (s, 1H), 6.78 (s, 1H), 3.89 (s, 3H), 3.84 (s, 3H), 3.48 (s, 2H), 3.17 (dd, 1H, J=8.0 Hz, J=17.6 Hz), 2.82-2.92 (m, 2H), 2.58-2.74 (m, 2H), 1.80-2.03 (m, 3H), 1.57-1.76 (m, 2H), 1.40-1.56 (m, 1H), 1.18-1.40 (m, 3H).

Workup

  1. extractionthe solution was extracted with 4×30 mL of ethyl acetate
  2. washwashed with 15 mL of Na2CO3 solution and with 15 mL NaCl solution
  3. dry with materialdried over anhydrous MgSO4
  4. customDrying agent
  5. filtrationwas then filtered off
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-7f927ac82d1f46a294354aab18796881
Source dataset
uspto-grants-2012_11
Patent number
US08318942B2

Reaction notes

Loading…