Methanol → 1-isopropylamino-2,3-dihydro-4-methoxy-1H-indene

HRID 1741419Notes

Reaction equation

HRID 1741419 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH2:6][C:7]2=O.[CH:13]([NH2:16])([CH3:15])[CH3:14].CO>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[CH:13]([NH:16][CH:7]1[C:8]2[C:4](=[C:3]([O:2][CH3:1])[CH:11]=[CH:10][CH:9]=2)[CH2:5][CH2:6]1)([CH3:15])[CH3:14]

Participants

6

Reactant 3

HCID 887MethanolHCID 6363IsopropylamineHCID 45474914-methoxy-2,3-dihydro-1H-inden-1-one

Product 1

HCID 183672411-isopropylamino-2,3-dihydro-4-methoxy-1H-indene

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-methoxy-1-indanone (0.71 g) and iso-propylamine (8 ml) in dichloromethane (10 ml) was added 1M solution of titanium(IV) chloride in dichloromethane (11 ml) at -60° C. for 15 minutes. The reaction mixture was stirred for 3 hours at the same temperature. Methanol (15 ml) was added to the reaction mixture. After being stirred for 2 hours at room temperature, the solution was evaporated in vacuo. The residue was partitioned between ethyl acetate and 1N aqueous NaOH solution. The insoluble material was filtered off by zeolite. The organic layer was washed with brine. The dried solvent was evaporated in vacuo to give 1-isopropylamino-2,3-dihydro-4-methoxy-1H-indene (0.89 g). MS (m/z): 206 (M+ +1) NMR (CDCl3, δ): 7.18 (1H, dd, J=7.8, 7.8 Hz), 6.97 (1H, d, J=7.8 Hz), 6.71 (1H, d, J=7.8 Hz), 4.30 (1H, t, J=6.7 Hz), 3.83 (3H, s), 3.20-2.87 (2H, m), 2.80-2.60 (1H, m), 2.50-2.35 (1H, m), 2.00-1.68 (1H, m), 1.13 (3H, d, J=6.9 Hz), 1.12 (3H, d, J=6.9 Hz)

Workup

  1. stirringAfter being stirred for 2 hours at room temperature
  2. customthe solution was evaporated in vacuo
  3. customThe residue was partitioned between ethyl acetate and 1N aqueous NaOH solution
  4. filtrationThe insoluble material was filtered off by zeolite
  5. washThe organic layer was washed with brine
  6. customThe dried solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-e3bf683236f240259165f6681f0fd040
Source dataset
uspto-grants-1999_10
Patent number
US05972965

Reaction notes

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