Triethylamine → HCID 21404986, compound

HRID 267871Notes

Reaction equation

HRID 267871 reaction equation
[CH2:1]([NH2:12])[CH2:2][C:3]1[CH:11]=[CH:10][C:9]2[O:8][CH2:7][O:6][C:5]=2[CH:4]=1.C(N(CC)CC)C.[C:20]12([C:30](Cl)=[O:31])[CH2:29][CH:24]3[CH2:25][CH:26]([CH2:28][CH:22]([CH2:23]3)[CH2:21]1)[CH2:27]2>C(OCC)C>[CH2:7]1[O:8][C:9]2[CH:10]=[CH:11][C:3]([CH2:2][CH2:1][NH:12][C:30]([C:20]34[CH2:29][CH:24]5[CH2:23][CH:22]([CH2:28][CH:26]([CH2:25]5)[CH2:27]3)[CH2:21]4)=[O:31])=[CH:4][C:5]=2[O:6]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 738741,3-Benzodioxole-5-ethanamineHCID 989151-Adamantanecarbonyl chloride

Product 1

HCID 21404986HCID 21404986, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Dissolve 0.5 g. of homopiperonylamine in 5 ml. of ethyl ether and 2.5 ml. of triethylamine. The mixture is cooled in an ice-bath and a solution of 0.6 g. of 1-adamantane carboxylic acid chloride in 10 ml. of ethyl ether added dropwise. Stir the mixture for an additional 3 hours. Add water and extract the mixture with ethyl acetate. Wash the ethyl acetate extract with 2N hydrochloric acid, saturated sodium bicarbonate solution, and water. Dry over anhydrous sodium sulfate, filter and evaporate the filtrate to a residue. Crystallize the residue from ethyl acetate to obtain the product of this step, m.p. 146°-148°C.

Workup

  1. dissolutionDissolve 0.5 g
  2. temperatureThe mixture is cooled in an ice-bath
  3. extractionAdd water and extract the mixture with ethyl acetate
  4. washWash the ethyl acetate
  5. extractionextract with 2N hydrochloric acid, saturated sodium bicarbonate solution, and water
  6. dry with materialDry over anhydrous sodium sulfate
  7. filtrationfilter
  8. customevaporate the filtrate to a residue
  9. customCrystallize the residue from ethyl acetate
  10. customto obtain the product of this step, m.p. 146°-148°C.

Sources & evidence

ORD record
ord-1c5d5ebf80754aedbf34cea4d764c324
Source dataset
uspto-grants-1976_03
Patent number
US03944675

Reaction notes

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