Methyl iodide → 1-[N-methyl-N-[(4,5-diphenyloxazol-2-yl)methyl]amino]-2,3-dihydro-4-methoxy-1H-indene

HRID 1741371Notes

Reaction equation

HRID 1741371 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([CH2:18][NH:19][CH:20]3[C:28]4[C:23](=[C:24]([O:29][CH3:30])[CH:25]=[CH:26][CH:27]=4)[CH2:22][CH2:21]3)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CI.[C:33]([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:33][N:19]([CH:20]1[C:28]2[C:23](=[C:24]([O:29][CH3:30])[CH:25]=[CH:26][CH:27]=2)[CH2:22][CH2:21]1)[CH2:18][C:9]1[O:10][C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:8]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 183673131-(4,5-diphenyloxazol-2-yl)methylamino-2,3-dihydro-4-methoxy-1H-indene

Product 1

HCID 183674131-[N-methyl-N-[(4,5-diphenyloxazol-2-yl)methyl]amino]-2,3-dihydro-4-methoxy-1H-indeneYield 69.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(4,5-diphenyloxazol-2-yl)methylamino-2,3-dihydro-4-methoxy-1H-indene (0.18 g) and methyl iodide (85 mg) in DMF (3 ml) was added K2CO3 (0.12 g). After being stirred for 16 hours, the solution was extracted with ethyl acetate. The mixture was washed with brine, dried over MgSO4 and evaporated in vacuo. The residue was purified by chromatography on silica gel to afford 1-[N-methyl-N-[(4,5-diphenyloxazol-2-yl)methyl]amino]-2,3-dihydro-4-methoxy-1H-indene (0.13 g). MS (m/z): (M+ +1) NMR (CDCl3, δ): 2.02-2.28 (1H, m), 2.44 (3H, s), 2.64-3.17 (3H, m), 3.82 (5H, s), 4.60 (1H, br), 6.73 (1H, d, J=7.9 Hz), 7.08-7.32 (2H, m), 7.32-7.48 (6H, m), 7.58-7.72 (4H, m)

Workup

  1. extractionthe solution was extracted with ethyl acetate
  2. washThe mixture was washed with brine
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo
  5. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-d2ac0fdb8072456086a6c7e4d27052dc
Source dataset
uspto-grants-1999_10
Patent number
US05972965

Reaction notes

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