Water → 1-[3-(2,3-Dihydro-1,4-benzodioxin-2-yl)propyl]-4-phenylpiperidin-4-ol

HRID 441420Notes

Reaction equation

HRID 441420 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][CH:2]1[CH2:11][CH2:12][C:13]([N:15]1[CH2:20][CH2:19][C:18]([OH:27])([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:17][CH2:16]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1.C(OCC)(=O)C>[OH:27][C:18]1([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:19][CH2:20][N:15]([CH2:13][CH2:12][CH2:11][CH:2]2[O:1][C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=3[O:4][CH2:3]2)[CH2:16][CH2:17]1

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 21331974HCID 21331974, compound

Product 1

HCID 213319551-[3-(2,3-Dihydro-1,4-benzodioxin-2-yl)propyl]-4-phenylpiperidin-4-ol

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

The solution of 5 g of 1-[3-(1,4-benzodioxan-2-yl)-propionyl]-4-hydroxy-4-phenylpiperidine in 50 ml of tetrahydrofuran is added to the stirred mixture of 2 g of lithium aluminum hydride and 50 ml of tetrahydrofuran at room temperature. Stirring is continued for 12 hours, whereupon the reaction mixture is decomposed with a few drops of ethyl acetate, 2 ml of water, 4 ml of 15% aqueous sodium hydroxide and 4 ml of water. It is filtered, the filtrate evaporated and the residue recrystallized from isopropanol, to yield the 2-[3-(4-hydroxy-4-phenylpiperidino)propyl]-1,4-benzodioxan melting at 95°-98°. The hydrochloride thereof is prepared in the above illustrated manner and recrystallized from isopropanol, mp. 155°-157°.

Workup

  1. filtrationIt is filtered
  2. customthe filtrate evaporated
  3. customthe residue recrystallized from isopropanol

Sources & evidence

ORD record
ord-7036041c44004a7dbcc7522ca4cc122e
Source dataset
uspto-grants-1977_08
Patent number
US04039676

Reaction notes

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