Water → HCID 9826565, compound

HRID 1781515Notes

Reaction equation

HRID 1781515 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:34](=[CH:35][CH:36]=1)[CH2:33][C:8]1([CH2:13][CH2:12][CH2:11][CH2:10][N:9]1[CH2:14][CH2:15][CH2:16][C:17]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:18][C:19]#[N:20])[CH2:7][CH2:6]2.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:34](=[CH:35][CH:36]=1)[CH2:33][C:8]1([CH2:13][CH2:12][CH2:11][CH2:10][N:9]1[CH2:14][CH2:15][CH2:16][C:17]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[CH2:18][CH2:19][NH2:20])[CH2:7][CH2:6]2

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 19045803HCID 19045803, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 9826565HCID 9826565, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3,4-dihydro-6-methoxy-1'-(5-cyano-4,4-diphenylpentyl)spiro[naphthalene-2(1H),2'-piperidine] (0.6 g) in tetrahydrofuran (15 ml) was added lithium aluminum hydride (95 mg) portionwise under ice-cooling and stirring. After completion of dropwise addition, the mixture was heated at 60° C. for 6 hours. To this reaction mixture were serially added water (0.25 ml), 15% sodium hydroxide solution (0.75 ml) and water (0.25 ml) under ice-cooling and stirring and the precipitate which separated out was filtered off. The filtrate was washed with saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and concentrated to dryness to provide the title compound (0.54 g) as light-yellow syrup.

Workup

  1. temperaturecooling
  2. additionAfter completion of dropwise addition
  3. temperaturecooling
  4. stirringstirring
  5. customthe precipitate which separated out
  6. filtrationwas filtered off
  7. washThe filtrate was washed with saturated aqueous solution of sodium chloride
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-dd8d9889812644d1ab380e5a374a299b
Source dataset
uspto-grants-1997_05
Patent number
US05633248

Reaction notes

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