Hydrochloric Acid → HCID 22033105, compound

HRID 1792295Notes

Reaction equation

HRID 1792295 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH2:15][N:16]2[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][O:24][C:25]3[CH:30]=[CH:29][C:28]([CH:31]4[C:40]5[C:35](=[CH:36][C:37]([O:41]COC)=[CH:38][CH:39]=5)[O:34][CH2:33][C:32]4([C:46]4[CH:51]=[CH:50][C:49]([O:52]COC)=[CH:48][CH:47]=4)[CH3:45])=[CH:27][CH:26]=3)[CH2:18][CH2:17]2)[CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].Cl.C(=O)(O)[O-].[Na+]>CO.ClCCl>[C:11]([C:9]1[CH:8]=[C:7]([CH2:15][N:16]2[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][O:24][C:25]3[CH:30]=[CH:29][C:28]([CH:31]4[C:40]5[C:35](=[CH:36][C:37]([OH:41])=[CH:38][CH:39]=5)[O:34][CH2:33][C:32]4([C:46]4[CH:47]=[CH:48][C:49]([OH:52])=[CH:50][CH:51]=4)[CH3:45])=[CH:27][CH:26]=3)[CH2:18][CH2:17]2)[CH:6]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:10]=1)([CH3:12])([CH3:13])[CH3:14]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 22033064HCID 22033064, compound

Product 1

HCID 22033105HCID 22033105, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

(3RS,4SR)-4-{4-{2-{4-{[3,5-Bis(t-butyl)phenyl]methyl}piperazinyl}ethoxy}phenyl}-7-(methoxymethoxy)-3-[4-(methoxymethoxy)phenyl]-3-methylchroman (150 mg, 0.21 mmol) was dissolved in methanol (1.5 ml), 6N-HCl (2 ml) was added portionwise thereto, and the mixture was stirred at 50–60° C. for 2 hours. The reaction solution was diluted with dichloromethane, which was then basified with saturated sodium bicarbonate solution. This solution was washed with water, dried over sodium sulfate, and filtered. The filtrate was evaporated under reduced pressure, and the concentrate thus obtained was subjected to silica gel column chromatography (dichloromethane:methanol=40:1) to give 75 mg (yield: 54%) of a pale yellow solid.

Workup

  1. washThis solution was washed with water
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customThe filtrate was evaporated under reduced pressure
  5. concentrationthe concentrate thus
  6. customobtained

Sources & evidence

ORD record
ord-9084cee2c4444cc081748c35eeb32eb2
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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