Aluminum isopropoxide → HCID 18740730, compound

HRID 1576259Notes

Reaction equation

HRID 1576259 reaction equation
O[CH:2]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:9]2([CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]2)[C:8]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]1=2.CC(C)[O-].[Al+3].CC(C)[O-].CC(C)[O-]>CC(C)=O>[CH3:15][N:12]1[CH2:11][CH2:10][C:9]2([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=3[CH2:2][C:3]3[C:8]2=[CH:7][CH:6]=[CH:5][CH:4]=3)[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 11143Aluminum isopropoxideHCID 86733944HCID 86733944, compound

Product 1

HCID 18740730HCID 18740730, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
220 °C

Procedure

10-Hydroxy-1'-methyl-9,10-dihydroanthracene-9-spiro-4'-piperidine (whose preparation is described in Example 2) (1 g.) and aluminium isopropoxide (3.1 g.) are thoroughly mixed and heated to 220°C. When acetone ceases to distil off the reaction mixture is heated to 225°C. for 40 minutes and then allowed to cool. Concentrated hydrochloric acid (7 ml.) in water (10 ml.) is added and the mixture is stirred for 30 minutes, basified with 2N sodium hydroxide and extracted with ethyl acetate. The organic layer is dried (Na2SO4) and evaporated to give a gum which crystallises on trituration with ether and is recrystallised twice from ether-petroleum ether (b.p. 40°- 60°C.) to give 1'-methyl-9,10-dihydroanthracene-9-spiro-4'-piperidine m.p. 132°-134°C.

Workup

  1. customto distil off the reaction mixture
  2. temperatureis heated to 225°C. for 40 minutes
  3. temperatureto cool
  4. additionConcentrated hydrochloric acid (7 ml.) in water (10 ml.) is added
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layer is dried (Na2SO4)
  7. customevaporated
  8. customto give a gum which
  9. customcrystallises on trituration with ether
  10. customis recrystallised twice from ether-petroleum ether (b.p. 40°- 60°C.)

Sources & evidence

ORD record
ord-309e17f8020846aa939fab5b7dfabeb1
Source dataset
uspto-grants-1976_09
Patent number
US03979513

Reaction notes

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