Sodium Hydroxide → HCID 86733954, compound

HRID 1576268Notes

Reaction equation

HRID 1576268 reaction equation
C([N:3]1[CH2:8][CH2:7][C:6]2([C:21]3[CH:20]=[CH:19][CH:18]=[C:17]([O:22][CH3:23])[C:16]=3[CH2:15][C:14]3[C:9]2=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:5][CH2:4]1)#N.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].[C:32]([OH:39])(=[O:38])/[CH:33]=[CH:34]\[C:35]([OH:37])=[O:36]>O1CCCC1.CCOCC.C(OCC)(=O)C.O>[C:32]([OH:39])(=[O:38])/[CH:33]=[CH:34]\[C:35]([OH:37])=[O:36].[CH3:23][O:22][C:17]1[C:16]2[CH2:15][C:14]3[C:9]([C:6]4([CH2:7][CH2:8][NH:3][CH2:4][CH2:5]4)[C:21]=2[CH:20]=[CH:19][CH:18]=1)=[CH:10][CH:11]=[CH:12][CH:13]=3

Participants

9

Reactant 4

HCID 14798Sodium HydroxideHCID 444266Maleic AcidHCID 21226445Aluminium lithium hydrideHCID 86733956HCID 86733956, compound

Product 1

HCID 86733954HCID 86733954, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

1'-Cyano-4-methoxy-9,10-dihydroanthracene-9-spiro-4'-piperidine (2.3 g.) in dry tetrahydrofuran (20 ml.) is added dropwise with stirring to a solution of lithium aluminium hydride (1 g.) in dry ether (200 ml.). When addition is complete the solution is stirred and heated under reflux for 1 hour. It is then allowed to cool and water (1 ml.), sodium hydroxide solution (1 ml., 2N), water (3 ml.), and ether (100 ml.) are added in succession and the suspension is stirred for 10 minutes and then filtered. The filtrate is washed with water and with brine, dried (MgSO4), and evaporated to give an oil which is taken up in the minimum volume of ethyl acetate and treated with a saturated solution of maleic acid in ethyl acetate. The precipitated solid is collected and recrystallised twice from isopropanol-ether to give 4-methoxy-9,10-dihydroanthracene-9-spiro-4'-piperidine maleate, m.p. 163°-165°C.

Workup

  1. additionWhen addition
  2. temperatureheated
  3. temperatureunder reflux for 1 hour
  4. temperatureto cool
  5. stirringthe suspension is stirred for 10 minutes
  6. filtrationfiltered
  7. washThe filtrate is washed with water and with brine
  8. dry with materialdried (MgSO4)
  9. customevaporated
  10. customto give an oil which
  11. customThe precipitated solid is collected
  12. customrecrystallised twice from isopropanol-ether

Sources & evidence

ORD record
ord-d9448af0d04e4096994fb31aa8bdaa29
Source dataset
uspto-grants-1976_09
Patent number
US03979513

Reaction notes

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