Diethyl Ether → HCID 703889, compound

HRID 267869Notes

Reaction equation

HRID 267869 reaction equation
[CH:1]1([C:7](Cl)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(OCC)C.[CH2:15]([NH2:27])[CH2:16][C:17]1[CH:26]=[CH:25][C:22]([O:23][CH3:24])=[C:19]([O:20][CH3:21])[CH:18]=1.C(N(CC)CC)C>C(OCC)(=O)C.O>[CH3:21][O:20][C:19]1[CH:18]=[C:17]([CH2:16][CH2:15][NH:27][C:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:8])[CH:26]=[CH:25][C:22]=1[O:23][CH3:24]

Participants

7

Reactant 4

HCID 3283Diethyl Ether2×HCID 8421HomoveratrylamineHCID 8471TriethylamineHCID 75938Cyclohexanecarbonyl chloride

Product 1

HCID 703889HCID 703889, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 2.0 g. of cyclohexane carboxylic acid chloride in 10 ml. of ethyl ether and add to a previously prepared solution of 2.0 g. of homoveratrylamine in a mixture of 20 ml. of ethyl ether and 5.0 ml. of triethylamine. Stir the mixture for 15 minutes, then add 20 ml. of water and 25 ml. of ethyl acetate. Separate the layers and extract the aqueous layers several times with ethyl acetate. Combine the organic phases and wash with 2N hydrochloric acid, saturated sodium bicarbonate solution and water. Dry the organic layer over anhydrous sodium sulfate, filter and evaporate to a residue. Crystallize the residue from ethyl acetate to obtain the product of this step, m.p. 110°-111°C.

Workup

  1. dissolutionDissolve 2.0 g
  2. additionadd 20 ml
  3. customSeparate the layers
  4. extractionextract the aqueous layers several times with ethyl acetate
  5. washwash with 2N hydrochloric acid, saturated sodium bicarbonate solution and water
  6. dry with materialDry the organic layer over anhydrous sodium sulfate
  7. filtrationfilter
  8. customevaporate to a residue
  9. customCrystallize the residue from ethyl acetate
  10. customto obtain the product of this step, m.p. 110°-111°C.

Sources & evidence

ORD record
ord-86f7fa10566e45b082d857f994a647c2
Source dataset
uspto-grants-1976_03
Patent number
US03944675

Reaction notes

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