Acetic Acid → HCID 86734269, compound

HRID 1973460Notes

Reaction equation

HRID 1973460 reaction equation
[CH:1]([NH:4][CH2:5][CH2:6][NH2:7])([CH3:3])[CH3:2].[OH:8][C:9]1[CH:24]=[CH:23][C:12]([C:13](=O)[CH2:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][C:16]2=O)=[CH:11][CH:10]=1.C(O)(=O)C>O.CCOCC>[OH:8][C:9]1[CH:24]=[CH:23][C:12]([C:13]2[N:7]([CH2:6][CH2:5][NH:4][CH:1]([CH3:3])[CH3:2])[C:16]3[CH2:17][CH2:18][CH2:19][CH2:20][C:15]=3[CH:14]=2)=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 88098N-IsopropylethylenediamineHCID 12270333Cyclohexanone, 2-[2-(4-hydroxyphenyl)-2-oxoethyl]-

Product 1

HCID 86734269HCID 86734269, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 7.25 g (0.071 mole) of isopropylaminoethylamine, 16.5 g (0.071 mole) of 2-(p-hydroxyphenacyl)cyclohexanone and acetic acid is refluxed under nitrogen for 6 hours, then cooled to ambient temperature, and diluted with water. The aqueous solution is washed with ether, then basified with 10% sodium carbonate and extracted with chloroform. The chloroform solution is washed with saturated sodium chloride solution, treated with charcoal, and dried over magnesium sulfate. The chloroform is removed to give a yellow solid which is recrystallized from acetonitrile to give a yellow-tan solid. The solid is dissolved in ether, the solution is filtered and concentrated to give 2-(p-hydroxyphenyl-1-(2-isopropylaminoethyl)-4,5,6,7-tetrahydroindole as a pale yellow solid, m.p. 149°-150° C.

Workup

  1. washThe aqueous solution is washed with ether
  2. extractionextracted with chloroform
  3. washThe chloroform solution is washed with saturated sodium chloride solution
  4. additiontreated with charcoal
  5. dry with materialdried over magnesium sulfate
  6. customThe chloroform is removed
  7. customto give a yellow solid which
  8. customis recrystallized from acetonitrile
  9. customto give a yellow-tan solid
  10. filtrationthe solution is filtered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-d4aa461fe9f6455985e7120ddab2002f
Source dataset
uspto-grants-1976_12
Patent number
US03997557

Reaction notes

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