Acetic Acid → HCID 10572092, compound

HRID 964012Notes

Reaction equation

HRID 964012 reaction equation
[OH-].[K+].Cl.Cl.[CH3:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH2:18][CH2:17][CH:16]([CH2:19][NH:20][CH2:21][CH:22]2[O:27][C:26]3[C:28]([O:32]S(C4C=CC(C)=CC=4)(=O)=O)=[CH:29][CH:30]=[CH:31][C:25]=3[O:24][CH2:23]2)[CH2:15][CH2:14]1.C(O)(=O)C>O.C(O)C>[OH:32][C:28]1[C:26]2[O:27][CH:22]([CH2:21][NH:20][CH2:19][CH:16]3[CH2:15][CH2:14][N:13]([C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=4[O:6][CH3:5])[CH2:18][CH2:17]3)[CH2:23][O:24][C:25]=2[CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14797Potassium HydroxideHCID 86752779HCID 86752779, compound

Product 1

HCID 10572092HCID 10572092, compoundYield 212.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of potassium hydroxide (1. 0 g) in water (19.7 ml) and ethanol (19.7 ml) was added in portions (~10 ml) at 15 minute intervals to [2-({[1-(2-methoxyphenyl)piperid-4-yl]methylamino}methyl)-1,4-benzodioxan-8-yl]toluene-4-sulphonate dihydrochloride (0.15 g). The mixture was heated under reflux for 21/2 hours, cooled and neutralised with glacial acetic acid. The product was extracted into ether (3×100 ml) and the combined extracts allowed to stand for 16 hours. The precipitate which had then formed was collected by filtration and dried to give N-(8-hydroxy-1,4-benzodioxan-2-ylmethyl) -1-[1-(2-methoxyphenyl) piperid-4-yl]methylamine as a colourless solid (0.2 g), m.p. 116°-119° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 21/2 hours
  3. extractionThe product was extracted into ether (3×100 ml)
  4. customThe precipitate which had then formed
  5. filtrationwas collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-22ee0bf1db124c76acaf5f829b0f4869
Source dataset
uspto-grants-1998_06
Patent number
US05767116

Reaction notes

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