1H-Indene, 2-methyl- → 2-methyl-3-(2-ethyl N-morpholinyl)indene

HRID 486404

Reaction equation

HRID 486404 reaction equation
[CH3:1][C:2]1[CH2:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.[CH2:11]([Li])[CH2:12][CH2:13][CH3:14].C1C2C(=CC=CC=2)C=C1.CCOCC.ClCC[N:33]1CC[O:36][CH2:35][CH2:34]1.[Cl-].[NH4+]>CCOCC.CCCCCC>[CH3:1][C:2]1[CH2:10][C:9]2[C:4]([C:3]=1[N:33]1[CH2:34][CH2:35][O:36][CH:12]([CH2:13][CH3:14])[CH2:11]1)=[CH:5][CH:6]=[CH:7][CH:8]=2

Participants

8

Reactant 5

HCID 165871H-Indene, 2-methyl-HCID 25517Ammonium ChlorideHCID 767274-(2-Chloroethyl)morpholineHCID 86747629Indene etherHCID 178418339Butyllithium

Product 1

HCID 190955172-methyl-3-(2-ethyl N-morpholinyl)indeneYield 54%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Procedure

16.4 g (0.126 mol) 2-methylindene was taken up in 150 ml dry ether under nitrogen atmosphere. A solution of 9.6 g (0.15 mol) n-butyl lithium (2.1 M) in hexane (62 ml) was added dropwise to the indene/ether solution. The resulting solution was stirred at room temperature for 2 hours and a solution of 3.5 g (0.18 mol) N-(2-chloroethyl)morpholine in 100 ml ether was added and stirred overnight. Saturated solution of ammonium chloride was added to the reaction mixture and the ether layer was extracted with 2N HCl. The acidic aqueous layer was then washed with ether twice and cooled in an ice bath, then neutralized with 35% sodium hydroxide and extracted with ether to give 16.3 g (54%) of the 2-methyl-3-(2-ethyl N-morpholinyl)indene (Formula II Rz=methyl; R3=R4=hydrogen; Alk=1,2-ethylene).

Workup

  1. stirringstirred overnight
  2. extractionthe ether layer was extracted with 2N HCl
  3. washThe acidic aqueous layer was then washed with ether twice
  4. temperaturecooled in an ice bath
  5. extractionextracted with ether

Sources & evidence

ORD record
ord-eb9d12dd997142e6a29dbf2c6d24972e
Source dataset
uspto-grants-1994_03
Patent number
US05292736

Linked notes

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