Ethanol → HCID 10134582, compound

HRID 2054140Notes

Reaction equation

HRID 2054140 reaction equation
[N:1]1[C:6]2[NH:7][C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[NH:10][CH2:11][C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:16](=[O:19])([O-])[O-].[K+].[K+].[CH2:22](O)[CH3:23]>CN(C)C=O>[CH:8]1([C:23]2[CH:22]=[CH:5][C:4]([C:16]([N:10]3[C:9]4[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=4[NH:7][C:6]4[N:1]=[CH:2][CH:3]=[CH:4][C:5]=4[CH2:11]3)=[O:19])=[CH:3][CH:2]=2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:9]1

Participants

5

Reactant 3

HCID 702EthanolHCID 11430Potassium CarbonateHCID 110307606,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine

Product 1

HCID 10134582HCID 10134582, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A suspension of 4-cyclohexylbenzoic acid (1.30 g, 6.4 mmol) in thionyl chloride (6 mL) was heated at reflux for 30 minutes. After cooling, the thionyl chloride was removed in vacuo. The residue was dissolved in toluene and concentrated in vacuo to give the acid chloride as a golden oil. The acid chloride was then dissolved in N,N-dimethylformamide (5 mL) and slowly added to a solution of 6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine (1.0 g, 5.1 mmol) and potassium carbonate (0.77 g, 5.6 mmol) in N,N-dimethylformamide (15 mL). After stirring for one hour, the reaction was quenched with water and extracted with ethyl acetate. The organic extracts were washed with 1 N sodium hydroxide, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give a light pink solid. The solid was dissolved in a large volume of boiling ethanol and filtered hot. The title compound (1.19 g) crystallized as an off-white solid, m.p. 230-233° C.

Workup

  1. customthe reaction was quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe organic extracts were washed with 1 N sodium hydroxide
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a light pink solid
  8. filtrationfiltered hot
  9. customThe title compound (1.19 g) crystallized as an off-white solid, m.p. 230-233° C.

Sources & evidence

ORD record
ord-efb496544dce43f6a454756ffa18927c
Source dataset
uspto-grants-2008_02
Patent number
US07329653B2

Reaction notes

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