Hydrochloric Acid → HCID 22123627, compound

HRID 1859346Notes

Reaction equation

HRID 1859346 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][N:31]4[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]4)=[CH:22][CH:21]=3)[C:7]([C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=3)([CH3:12])[CH2:8][S:9]2)=[CH:4][CH:3]=1.[ClH:37]>CO>[ClH:37].[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][N:31]4[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]4)=[CH:22][CH:21]=3)[C:7]([C:13]3[CH:14]=[CH:15][C:16]([OH:19])=[CH:17][CH:18]=3)([CH3:12])[CH2:8][S:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22123628HCID 22123628, compound

Product 1

HCID 22123627HCID 22123627, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To methanol solution (3 ml) of (3RS,4RS)-7-hydroxy-3-(4-hydroxyphenyl)-3-methyl-4-[4-(4-piperidinobutyloxy)phenyl]thiochroman (18 mg, 0.093 mmol) was added aqueous 20% HCl solution (0.3 ml) and the resulting mixture was stirred for 20 hours. The reaction solution was distilled under reduced pressure to remove the solvent and the crude product thus produced was dissolved in methanol. To the resulting solution was added Dowex 1-×8 (240 mg) and the mixture was stirred for 30 minutes. Dowex 1-×8 was filtered off and the filtrate was then distilled under reduced pressure to remove the solvent. To the residue were added toluene (0.5 ml), methanol (0.5 ml) and 35% HCl (0.5 ml) and the mixture was distilled under reduced pressure to obtain 17 mg (yield: 96%) of the title compound.

Workup

  1. distillationThe reaction solution was distilled under reduced pressure
  2. customto remove the solvent
  3. customthe crude product thus produced
  4. stirringthe mixture was stirred for 30 minutes
  5. filtrationDowex 1-×8 was filtered off
  6. distillationthe filtrate was then distilled under reduced pressure
  7. customto remove the solvent
  8. additionTo the residue were added toluene (0.5 ml), methanol (0.5 ml) and 35% HCl (0.5 ml)
  9. distillationthe mixture was distilled under reduced pressure

Sources & evidence

ORD record
ord-a34186026587462a98a0f4f4260036dc
Source dataset
uspto-grants-2000_11
Patent number
US06153768

Reaction notes

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