1,2-Ethanediamine, N1,N1-bis(1-methylethyl)- → HCID 23456456, compound

HRID 1973461Notes

Reaction equation

HRID 1973461 reaction equation
[CH:1]([N:4]([CH2:8][CH2:9][NH2:10])[CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2].[OH:11][C:12]1[CH:27]=[CH:26][C:15]([C:16](=O)[CH2:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][C:19]2=O)=[CH:14][CH:13]=1>C(O)(=O)C.O.Cl>[CH:1]([N:4]([CH:5]([CH3:7])[CH3:6])[CH2:8][CH2:9][N:10]1[C:19]2[CH2:20][CH2:21][CH2:22][CH2:23][C:18]=2[CH:17]=[C:16]1[C:15]1[CH:14]=[CH:13][C:12]([OH:11])=[CH:27][CH:26]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 84591,2-Ethanediamine, N1,N1-bis(1-methylethyl)-HCID 12270333Cyclohexanone, 2-[2-(4-hydroxyphenyl)-2-oxoethyl]-

Product 1

HCID 23456456HCID 23456456, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

A solution of 5.77 g (0.04 mole) of diisopropylaminoethylamine and 9.3 g (0.04 mole) of 2-(p-hydroxyphenacyl) cyclohexanone in glacial acetic acid is refluxed under nitrogen for 14 hours, then cooled to ambient temperature and diluted with water and dilute hydrochloric acid. The aqueous solution is washed with ether, basified with 10% sodium carbonate and extracted with ether. After drying the ether solution over magnesium sulfate, the ether is removed to give a pale yellow solid. The solid is recrystallized from an ether-petroleum ether mixture to give pale yellow crystals of 1-(2-diisopropylaminoethyl)-2-(p-hydroxyphenyl)-4,5,6,7-tetrahydroindole as pale yellow crystals, m.p. 112°-114.5° C.

Workup

  1. washThe aqueous solution is washed with ether
  2. extractionextracted with ether
  3. dry with materialAfter drying the ether solution over magnesium sulfate
  4. customthe ether is removed
  5. customto give a pale yellow solid
  6. customThe solid is recrystallized from an ether-petroleum ether mixture

Sources & evidence

ORD record
ord-6088b8d70ba448e280fdd279b831cbeb
Source dataset
uspto-grants-1976_12
Patent number
US03997557

Reaction notes

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