Ethyl Acetate → HCID 86602388, compound

HRID 1375349Notes

Reaction equation

HRID 1375349 reaction equation
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH2:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:22][C:23]([N:25]1[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2[CH2:29][CH2:28][CH2:27][CH2:26]1)=[O:24].CCOC(C)=O>CN(C=O)C>[O:24]=[C:23]([N:25]1[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2[CH2:29][CH2:28][CH2:27][CH2:26]1)[CH2:22][NH:14][C:9]1[C:8]([NH:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 68297N-Phenyl-o-phenylenediamineHCID 58584388HCID 58584388, compound

Product 1

HCID 86602388HCID 86602388, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of N-phenyl-o-phenylene diamine (10 g, 54.3 mM) in 100 ml of DMF at RT was added K2CO3 (8.25 g, 60 mM) followed by 1-(bromoacetyl)-2,3,4,5-tetrahydro-1H-1-benzazepine (14.56 g 54.3 mM). The resulting mixture was stirred at RT until TLC (Hex:AcOEt 3:1) showed completion of reaction. The mixture was filtered to remove the K2CO3 and then diluted with 800 mL of EtOAc and 200 mL of Et2O. This solution was washed successively with H2O (2×400 mL), brine (1×400 mL), 1 N HCl (2×400 mL), and H2O (1×400 mL), and the organics dried (MgSO4) and concentrated to give a greenish-black oil. The resultant oil was purified by silica gel flash column chromatography using hexane/EtOAc4/1 and the combined filtrates evaporated in vacuo to give 20 g of product. 1H NMR (300 MHz, CDCl3) 1.25–1.40 (m, 1H), 1.66–2.00 (m, 3H), 2.55.2.75 (m, 2H), 2.88 (t, J=13 Hz, 1H), 3.54(d, J=17 Hz, 1H), 4.10 (d, J=17 Hz, 1H), 4.57 (m, 1H), 6.80–7.80 (m, 12H), 7.47 (m, 1H).

Workup

  1. customcompletion of reaction
  2. filtrationThe mixture was filtered
  3. customto remove the K2CO3
  4. additiondiluted with 800 mL of EtOAc and 200 mL of Et2O
  5. washThis solution was washed successively with H2O (2×400 mL), brine (1×400 mL), 1 N HCl (2×400 mL), and H2O (1×400 mL)
  6. dry with materialthe organics dried (MgSO4)
  7. concentrationconcentrated
  8. customto give a greenish-black oil
  9. customThe resultant oil was purified by silica gel flash column chromatography
  10. customthe combined filtrates evaporated in vacuo

Sources & evidence

ORD record
ord-04e69dd14fc848a0bf5d9a5ceb10acb0
Source dataset
uspto-grants-2007_01
Patent number
US07169773B2

Reaction notes

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