Hydrochloric Acid → HCID 46195901, compound

HRID 2360099Notes

Reaction equation

HRID 2360099 reaction equation
[CH:1]1[CH:10]=[C:9]([OH:11])[CH:8]=[C:7]2[C:2]=1[CH:3]1[O:14][C:13]3[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=3[CH:4]1[CH2:5][O:6]2.[H-].[Na+].Cl.Cl[CH2:23][CH2:24][N:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.Cl>CN(C=O)C.O>[CH:1]1[CH:10]=[C:9]([O:11][CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[CH:8]=[C:7]2[C:2]=1[CH:3]1[O:14][C:13]3[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=3[CH:4]1[CH2:5][O:6]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochlorideHCID 391074HCID 391074, compound

Product 1

HCID 46195901HCID 46195901, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Compound 6a,11a-dihydro-6H-benzo[4,5]furo[3,2-c]chromen-3-ol (100 mg, 0.42 mmol) was dissolved in DMF (5 ml) and NaH (10 mg, 0.42 mmol) was added to the solution at room temperature, followed by 1-(2-chloroethyl)piperidine hydrochloride (366 mg, 0.84 mmol). The reaction mixture was stirred at room temperature to 6 hours and poured into iced water and neutralized with 10% HCl to get the white precipitate. Precipitate were washed with water and purified by silica gel column chromatography using hexane-chloroform as the eluent to give 1-(2-(6a,11a-dihydro-6H-benzofuro[3,2-c]chromen-3-yloxy)ethyl)piperidine (102 mg, 70%) as white solid.

Workup

  1. customto get the white precipitate
  2. washPrecipitate were washed with water
  3. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-a0327d8ff8b84e709307ed77404cf039
Source dataset
uspto-grants-2014_04
Patent number
US08686028B2

Reaction notes

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