Diethyl Ether → 2-methyl-3-(2-ethyl N-morpholinyl)indene

HRID 486405Notes

Reaction equation

HRID 486405 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[CH2:10]([Li])[CH2:11][CH2:12][CH3:13].ClCC[N:18]1CC[O:21][CH2:20][CH2:19]1.[Cl-].[NH4+].[CH3:26]COCC>>[CH3:26][C:2]1[CH2:3][C:4]2[C:9]([C:1]=1[N:18]1[CH2:19][CH2:20][O:21][CH:11]([CH2:12][CH3:13])[CH2:10]1)=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

6

Reactant 5

HCID 3283Diethyl Ether3×HCID 7219IndeneHCID 25517Ammonium ChlorideHCID 767274-(2-Chloroethyl)morpholineHCID 178418339Butyllithium

Product 1

HCID 190955172-methyl-3-(2-ethyl N-morpholinyl)indeneYield 60%

Procedure

5.8 g (0.05 mol) indene was taken up in 50 mL dry ether under nitrogen. To this solution a solution of 2.303 g (0.05 mol) n-butyllithium (2.1 M) in 150 mL of ether was added dropwise. The solution was stirred at room temperature for 2 hours and a solution of 33.5 g (0.18 mol) N-(2-chloroethyl)morpholine was added and stirred overnight at room temperature. The reaction mixture was neutralized with saturated ammonium chloride solution and the ether layer separated and dried over magnesium sulfate and concentrated in vacuo giving a yellow oil. The product was redissolved in ether and extracted with 200 ml 2 N HCl twice. The aqueous layer was again extracted with ether and cooled in an ice bath. This cooled, acidic mixture was then slowly neutralized with 35% NaOH and extracted twice with ether. The organic layers were pooled and washed with water, saturated NaCl and dried over magnesium sulfate to give 6.9 g (60%) of the desired 3-[2-(4-morpholinyl)ethyl]indene (Formula II R2 =R3 =R4 =hydrogen; Alk=1,2-ethylene).

Workup

  1. stirringstirred overnight at room temperature
  2. customthe ether layer separated
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customgiving a yellow oil
  6. extractionextracted with 200 ml 2 N HCl twice
  7. extractionThe aqueous layer was again extracted with ether
  8. temperaturecooled in an ice bath
  9. extractionextracted twice with ether
  10. washwashed with water, saturated NaCl
  11. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-21b95b6ff8604424bcf6a542aa348f81
Source dataset
uspto-grants-1994_03
Patent number
US05292736

Reaction notes

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