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

HRID 1741418Notes

Reaction equation

HRID 1741418 reaction equation
[C:1]([N:4]([CH:23]1[C:31]2[C:26](=[C:27]([O:32][CH3:33])[CH:28]=[CH:29][CH:30]=2)[CH2:25][CH2:24]1)[CH2:5][C:6]1[O:7][C:8]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:10]=1)(=O)[CH3:2].Cl>C1COCC1>[CH2:1]([N:4]([CH:23]1[C:31]2[C:26](=[C:27]([O:32][CH3:33])[CH:28]=[CH:29][CH:30]=2)[CH2:25][CH2:24]1)[CH2:5][C:6]1[O:7][C:8]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:9]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:10]=1)[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 183674301-[N-acetyl-N-[(4,5-diphenyloxazol-2-yl)methyl]amino]-2,3-dihydro-4-methoxy-1H-indene

Product 1

HCID 183672641-[N-ethyl-N-[(4,5-diphenyloxazol-2-yl)methyl]amino]-2,3-dihydro-4-methoxy-1H-indeneYield 121.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-[N-acetyl-N-[(4,5-diphenyloxazol-2-yl)methyl]amino]-2,3-dihydro-4-methoxy-1H-indene (0.40 g) in THF (10 ml) was added 1M solution of borane-THF complex in THF (9 ml) at room temperature. The reaction mixture was refluxed for 8 hours and cooled down to room temperature. 1N aqueous HCl solution (25 ml) was added to the reaction mixture. After being stirred for 1 hour at room temperature, the mixture was partitioned between ethyl acetate and 1N aqueous NaOH solution. The organic layer was washed with brine. The dried solvent was evaporated in vacuo to give 1-[N-ethyl-N-[(4,5-diphenyloxazol-2-yl)methyl]amino]-2,3-dihydro-4-methoxy-1H-indene (0.47 g). MS (m/z): 425 (M+ +1) NMR (CDCl3, δ): 7.66-7.58 (4H, m), 7.39-7.08 (8H, m), 6.70 (1H, d, J=7.7 Hz), 4.67 (1H, t, J=7.6 Hz), 3.81 (3H, s), 3.18-2.80 (2H, m), 2.73 (2H, q, J=7.2 Hz), 2.35-1.84 (2H, m), 1.14 (3H, t, J=7.2 Hz)

Workup

  1. temperatureThe reaction mixture was refluxed for 8 hours
  2. customthe mixture was partitioned between ethyl acetate and 1N aqueous NaOH solution
  3. washThe organic layer was washed with brine
  4. customThe dried solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-11f001be355f42fb9847c27b06070a17
Source dataset
uspto-grants-1999_10
Patent number
US05972965

Reaction notes

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