1-Phenyl-1-propanone → 2-[3'-(N, N-dimethylamino)phenyl]-1-phenyl-1-propanone

HRID 595355Notes

Reaction equation

HRID 595355 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[N:5]([CH3:7])[CH3:6].[C:11]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:14])[CH2:12][CH3:13].C(O[Na])(C)(C)C>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.COC1C=CC=C(N(C)C2C=CC=CC=2)C=1P(C1CCCCC1)C1CCCCC1>[CH3:6][N:5]([C:4]1[CH:3]=[C:2]([CH:12]([CH3:13])[C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:14])[CH:10]=[CH:9][CH:8]=1)[CH3:7]

Participants

7

Reactant 3

HCID 71481-Phenyl-1-propanoneHCID 23285N,N-Dimethyl-3-chloroanilineHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 1176415812-[3'-(N, N-dimethylamino)phenyl]-1-phenyl-1-propanoneYield 79.2%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 71725627(2-Dicyclohexylphosphino-3-methoxy-N-methyl-N-phenylbenzenamineCatalystHCID 1140TolueneSolvent

Procedure

This reaction is carried out in the same manner as the reaction in example 3. The difference is that, the reactants are 3-chloro-N,N-dimethylaniline (155.9 mg, 1.0 mmol), propiophenone (160.9 mg, 1.2 mmol), palladium acetate (6.7 mg, 0.030 mmol), 2-Methoxy-6-(N-methyl-N-phenyl-amino)phenyl(dicyclohexyl)phosphine (18.4 mg, 0.045 mmol), t-BuONa (116.1 mg, 1.2 mmol) in 3 mL dry toluene at 110° C. for 11.5 h. 2-[3′-(N, N-dimethylamino)phenyl]-1-phenyl-1-propanone (200.7 mg) was obtained with a yield of 79% as liquid. 1H NMR (300 MHz, CDCl3) δ 8.03-7.97 (m, 2H, ArH), 7.52-7.44 (m, 1H, ArH), 7.43-7.35 (m, 2H, ArH), 7.20-7.11 (m, 1H, ArH), 6.65-6.55 (m, 3H, ArH), 4.19 (s, 2H, CH2), 2.87 (s, 6H, 2×CH3); 13C NMR (75 MHz, CDCl3) δ 197.7, 150.6, 136.4, 135.1, 132.8, 129.1, 128.5, 128.4, 117.4, 113.1, 110.9, 45.9, 40.3; IR (neat) v (cm−1) 3056, 2891, 2804, 1679, 1601, 1579, 1501, 1447, 1354, 1330, 1276, 1205, 1180, 1155, 1062; MS (70 eV, EI) m/z (%): 240 (M++1, 10.27), 239 (M+, 54.99), 105 (100); HRMS calcd for C16H17NO (M+): 239.1310. Found: 239.1309.

Workup

  1. customThis reaction is carried out in the same manner as the reaction in example 3
  2. customat 110° C.
  3. customfor 11.5 h

Sources & evidence

ORD record
ord-fe87a5d3c7314a9a8239acedfe0cc957
Source dataset
uspto-grants-2016_01
Patent number
US09243011B2

Reaction notes

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