Water → HCID 58230130, compound

HRID 2368805Notes

Reaction equation

HRID 2368805 reaction equation
[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][CH:6]=1)([CH3:3])[CH3:2].C([O:14][C:15]([C:17]1([CH2:24][CH2:25]OC)[CH2:22][CH2:21][CH:20]([OH:23])[CH2:19][CH2:18]1)=O)C.[Cl-].C[Al+]C.O>C1(C)C=CC=CC=1.CCOC(C)=O>[OH:23][CH:20]1[CH2:21][CH2:22][C:17]2([C:15](=[O:14])[N:11]([C:8]3[CH:9]=[CH:10][C:5]([O:4][CH:1]([CH3:3])[CH3:2])=[CH:6][CH:7]=3)[CH2:25][CH2:24]2)[CH2:18][CH2:19]1

Participants

7

Reactant 4

HCID 962WaterHCID 821124-IsopropoxyanilineHCID 16686359Dimethylalumanylium chlorideHCID 582299764-Hydroxy-1-(2-methoxy-ethyl)-cyclohexanecarboxylic acid ethyl ester

Product 1

HCID 58230130HCID 58230130, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

4-Isopropoxy-phenylamine (11.3 g) was added to a solution of 4-hydroxy-1-(2-methoxy-ethyl)-cyclohexanecarboxylic acid ethyl ester (11.5 g) in toluene (361 ml). The mixture was stirred for 10 minutes at RT. Then, dimethylaluminiumchloride (0.9 M in hexane, 99 ml) was added dropwise and the reaction mixture was heated to reflux for 4 h. The mixture was then cooled to 0° C., water (50 ml) was added dropwise then AcOEt (300 ml). The mixture was stirred further 30 minutes, more AcOEt was added, the layers were then separated, the organic layer was dried over MgSO4, filtered and the solvent was evaporated off. The crude product was triturated with diethyl ether/heptane to give the title compound as a mixture of cis/trans isomers as brown solid (14.3 g) which was used directly in the next step. MS (m/e): 304.190 [MH+].

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 4 h
  3. temperatureThe mixture was then cooled to 0° C.
  4. stirringThe mixture was stirred further 30 minutes
  5. customthe layers were then separated
  6. dry with materialthe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. customthe solvent was evaporated off
  9. customThe crude product was triturated with diethyl ether/heptane

Sources & evidence

ORD record
ord-20fad28c0eac49ed9658455aeea0f8b5
Source dataset
uspto-grants-2014_04
Patent number
US08703807B2

Reaction notes

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