Hydrochloric Acid → HCID 58230035, compound

HRID 2092703Notes

Reaction equation

HRID 2092703 reaction equation
C(O[C:4]([C:6]1([CH2:13][CH2:14]OC)[CH2:11][CH2:10][C:9](=[CH2:12])[CH2:8][CH2:7]1)=[O:5])C.[CH:17]1([C:20]2[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=2)[CH2:19][CH2:18]1.[Cl-].C[Al+]C.Cl>C1(C)C=CC=CC=1.O>[CH:17]1([C:20]2[CH:26]=[CH:25][C:23]([N:24]3[CH2:14][CH2:13][C:6]4([CH2:7][CH2:8][C:9](=[CH2:12])[CH2:10][CH2:11]4)[C:4]3=[O:5])=[CH:22][CH:21]=2)[CH2:19][CH2:18]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 122539274-CyclopropylanilineHCID 16686359Dimethylalumanylium chlorideHCID 58230019HCID 58230019, compound

Product 1

HCID 58230035HCID 58230035, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 0.3 g (1.3 mmol) 1-(2-methoxy-ethyl)-4-methylene-cyclohexanecarboxylic acid ethyl ester and 0.264 g (1.98 mmol) 4-cyclopropylaniline in 6 mL toluene was treated with 2.65 mL (2.65 mmol) dimethylaluminium chloride (1M in toluol) and stirred for 4 h at 100° C. After cooling to room temperature water and 1N HCl aq. was carefully added and the mixture poured onto water and extracted with ethyl acetate. The combined organic layers were washed with water, dried with MgSO4, filtered and evaporated to dryness. The residue was purified by flash column chromatography over silica eluting with a gradient formed from hexane and ethyl acetate to yield after evaporation of the product containing fractions 0.264 g (71%) of the title compound as yellow crystals. MS (m/e): 282.4 [MH+].

Workup

  1. additionwas carefully added
  2. additionthe mixture poured onto water
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were washed with water
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe residue was purified by flash column chromatography over silica eluting with a gradient
  9. customformed from hexane and ethyl acetate
  10. customto yield
  11. customafter evaporation of the product
  12. additioncontaining fractions 0.264 g (71%) of the title compound as yellow crystals

Sources & evidence

ORD record
ord-3b998c151e7143adadeff01ddc6f0d32
Source dataset
uspto-grants-2013_05
Patent number
US08440710B2

Reaction notes

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