Dichloromethane → HCID 57102782, compound

HRID 1792357Notes

Reaction equation

HRID 1792357 reaction equation
COC[O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]([C:26]3[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH:37]4[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]4)=[CH:28][CH:27]=3)[C:10]([C:16]3[CH:21]=[CH:20][C:19]([O:22]COC)=[CH:18][CH:17]=3)([CH3:15])[CH2:11][O:12]2)=[CH:7][CH:6]=1.C(Cl)Cl>CO>[OH:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]([C:26]3[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH:37]4[CH2:38][CH2:39][NH:40][CH2:41][CH2:42]4)=[CH:28][CH:27]=3)[C:10]([C:16]3[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=3)([CH3:15])[CH2:11][O:12]2)=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 69590093HCID 69590093, compound

Product 1

HCID 57102782HCID 57102782, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of (3RS,4RS)-7-methoxymethoxy-3-(4-(methoxymethoxy)phenyl)-3-methyl-4-[4-(4-piperidylbutyloxy)phenyl]chroman (325 mg, 0.56 mmol) p-toluenesulfonic acid (1.42 g, 5.6 mmol) and methanol was stirred at reflux 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 column chromatography (CH2Cl2:methanol=10:1) to give 160 mg (yield. 58%) of a white foamy solid.

Workup

  1. temperatureat reflux 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
  9. customto give
  10. custom160 mg (yield. 58%) of a white foamy solid

Sources & evidence

ORD record
ord-46de277a28f5426fa2317691a87066e3
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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