HCID 69669210, compound → Benzophenone, 4-amino-4'-(dimethylamino)-

HRID 1470566Notes

Reaction equation

HRID 1470566 reaction equation
[CH3:1][N:2]([CH3:25])[C:3]1[CH:24]=[CH:23][C:6]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([NH:15]C(=O)OC(C)(C)C)=[CH:11][CH:10]=2)=[O:8])=[CH:5][CH:4]=1>FC(F)(F)C(O)=O.ClCCl>[NH2:15][C:12]1[CH:11]=[CH:10][C:9]([C:7]([C:6]2[CH:23]=[CH:24][C:3]([N:2]([CH3:25])[CH3:1])=[CH:4][CH:5]=2)=[O:8])=[CH:14][CH:13]=1

Participants

4

Reactant 1

HCID 69669210HCID 69669210, compound

Product 1

HCID 165353Benzophenone, 4-amino-4'-(dimethylamino)-Yield 95%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

The compound 4 (51 mg, 0.15 mmol) was stirred in 10% trifluoroacetic acid (TFA) in dichloromethane (10 mL) at room temperature for 1 hour and extracted with ethyl acetate with aqueous NaHCO3. The organic layer was dried over Na2SO4, and the filtrate was concentrated to give intermediate B (34 mg, 95%). 1H-NMR (CDCl3) 7.76 (d, J=8.7, 2H), 7.66 (d, J=8.4, 2H), 6.68 (d, J=8.7, 2H), 6.67 (d, J=8.4, 2H), 4.04 (br. s, 1H), 3.06 (s, 6H) ppm; ESI-MS m/z calcd for C15H16N2O: 240. 3004. found 241.2071 [M+1].

Workup

  1. extractionextracted with ethyl acetate with aqueous NaHCO3
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-3b4560488ee64ee1958bf082b8e255c4
Source dataset
uspto-grants-2015_04
Patent number
US09006458B2

Reaction notes

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