Aniline → HCID 58897808, compound

HRID 2357865Notes

Reaction equation

HRID 2357865 reaction equation
[C:1]1([NH2:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li]CCCC.Br[C:14]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:15]=1[CH2:16][CH2:17][C:18]2([O:29][CH3:30])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1N(C)C)(C)(C)C>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].O>[CH3:30][O:29][C:18]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:19]2[CH:20]=[CH:21][CH:22]=[C:14]([NH:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:15]=2[CH2:16][CH2:17]1

Participants

8

Reactant 4

HCID 6115AnilineHCID 27349362-Di-tert-butylphosphino-2'-(N,N-dimethylamino)biphenylHCID 58897786HCID 58897786, compoundHCID 178418339Butyllithium

Product 1

HCID 58897808HCID 58897808, compound

Reagents, catalysts & solvents 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Under an argon atmosphere, to a solution of 4.56 ml (4.66 g, 50.0 mmol) of PhNH2 in 200 ml of toluene, 20.0 ml of 2.5 M nBuLi (50.0 mmol) in hexanes was added dropwise at ambient temperature. Then, hexanes were distilled off under vacuum. To the obtained suspension, 12.1 g (39.7 mmol) of 4-bromo-1-methoxy-1-phenylindane, 434 mg (0.76 mmol) of Pd(dba)2, and 503 mg (1.47 mmol) of N-{2′-[di(tert-butyl)phosphino][1,1′-biphenyl]-2-yl}-N,N-dimethylamine were added. This mixture was refluxed for 1 hour, then, 300 ml of water was added. The organic layer was separated; the aqueous layer was extracted with 3×75 ml of ether. The combined extract was dried over Na2SO4 and, then, evaporated to dryness. The analytically pure 1-methoxy-N,1-diphenyl-4-indanamine was obtained by flash chromatography on Silica Gel 60 (40-63 μm, d 50 mm, 1300 mm, eluant: CH2Cl2). Yield, 12.5 g (99%).

Workup

  1. distillationThen, hexanes were distilled off under vacuum
  2. temperatureThis mixture was refluxed for 1 hour
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with 3×75 ml of ether
  5. extractionThe combined extract
  6. dry with materialwas dried over Na2SO4
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-98cf49600d4445a2bdc4a7193abc8c47
Source dataset
uspto-grants-2010_07
Patent number
US07763562B2

Reaction notes

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