Hydrochloric Acid → HCID 18980499, compound

HRID 2392769Notes

Reaction equation

HRID 2392769 reaction equation
[CH3:1][N:2]([CH2:4][CH:5]1[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=2)([OH:15])[CH2:13][CH2:12][C:7]2(OCC[O:8]2)[CH2:6]1)[CH3:3].Cl.[OH-].[Na+]>O1CCCC1>[CH3:1][N:2]([CH2:4][CH:5]1[C:14]([OH:15])([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=2)[CH2:13][CH2:12][C:7](=[O:8])[CH2:6]1)[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18980507HCID 18980507, compound

Product 1

HCID 18980499HCID 18980499, compoundYield 54,081.602%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

78 g (0.24 mmole) 7-dimethylaminomethyl-8-(3-methoxy-phenyl)-1,4-dioxaspiro[4.5]decan-8-ol (65) were dissolved in a 500 ml tetrahydrofuran and cooled to a temperature between 0° C. and 5° C. 200 ml of aqueous hydrochloric acid (2:1 concentrated hydrochloric acid/water) were added over 30 minutes. The mixture was stirred for 12 hours at room temperature and was subsequently cooled to a temperature between 0° C. and 5° C. After adding 250 ml of concentrated aqueous sodium hydroxide solution the product was extracted three times with ether and dried over sodium sulphate. After removing the solvent by distillation, the residue (66 g) was introduced on to a silica gel column and eluted successively with diisopropyl ether, 1:1 diisopropyl ether/ether and 1:1 ethyl acetate/methanol. 36 g base (66) (48%% theoretical) were obtained as a light yellow, viscous oil.

Workup

  1. temperaturecooled to a temperature between 0° C. and 5° C
  2. temperaturewas subsequently cooled to a temperature between 0° C. and 5° C
  3. extractionwas extracted three times with ether
  4. dry with materialdried over sodium sulphate
  5. customAfter removing the solvent
  6. distillationby distillation
  7. additionthe residue (66 g) was introduced on to a silica gel column
  8. washeluted successively with diisopropyl ether, 1:1 diisopropyl ether/ether and 1:1 ethyl acetate/methanol

Sources & evidence

ORD record
ord-546aa1fec9aa4750b9b075d97d23d518
Source dataset
uspto-grants-1998_09
Patent number
US05801201

Reaction notes

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