Dichloromethane → HCID 69590093, compound

HRID 1792356Notes

Reaction equation

HRID 1792356 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][C:10]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH2:23][O:24][CH3:25])=[CH:18][CH:17]=3)([CH3:15])[CH2:11][O:12]2)=[CH:7][CH:6]=1.[NH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.C(Cl)Cl>CO>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]([C:6]3[CH:5]=[CH:14][C:13]([O:12][CH2:11][CH2:10][CH2:16][CH2:17][CH:29]4[CH2:30][CH2:31][NH:26][CH2:27][CH2:28]4)=[CH:8][CH:7]=3)[C:10]([C:16]3[CH:17]=[CH:18][C:19]([O:22][CH2:23][O:24][CH3:25])=[CH:20][CH:21]=3)([CH3:15])[CH2:11][O:12]2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 8082PiperidineHCID 54259996HCID 54259996, compound

Product 1

HCID 69590093HCID 69590093, compoundYield 150.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To (3RS,4RS)-4-[4-(4-chlorobutyloxy)phenyl]-(7-(methoxymethoxy)-3-(4-(methoxymethoxy)phenyl)-3-methylchroman (393 mg, 0.75 mmol) was added piperidine (738 mg, 7.5 mmol) and the mixture was refluxed for 12 h. After cooling, the mixture was extracted with ethyl acetate, dried over MgSO4, and filtered. The filtrate was evaporated under reduced pressure, and the concentrate thus obtained was subjected to silica gel columnchromatography (CH2Cl2:methanol=20:1) to give 325 mg (yield: 75%) of a colorless oil.

Workup

  1. temperaturethe mixture was refluxed for 12 h
  2. temperatureAfter cooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customThe filtrate was evaporated under reduced pressure
  7. concentrationthe concentrate thus
  8. customobtained

Sources & evidence

ORD record
ord-e8bf610a196742608cac70a9ef2c53bd
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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