N-methyl-2-pyrrolidone → HCID 12148789, compound

HRID 413548Notes

Reaction equation

HRID 413548 reaction equation
[C:1]1([CH:7]([O:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=3)=[CH:14][CH:13]=2)[CH2:8][CH2:9]Cl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH2:30]([O:32][C:33](=[O:37])[CH2:34][NH:35][CH3:36])[CH3:31].C(N(C(C)C)CC)(C)C.CN1CCCC1=O>O>[CH2:30]([O:32][C:33](=[O:37])[CH2:34][N:35]([CH3:36])[CH2:9][CH2:8][CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[O:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=2)=[CH:14][CH:13]=1)[CH3:31]

Participants

6

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 171173Ethyl N-methylaminoacetate hydrochlorideHCID 12148787HCID 12148787, compound

Product 1

HCID 12148789HCID 12148789, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
92.5 °C

Procedure

To a 125 mL round-bottomed flask equipped with condenser and nitrogen inlet were added 486 mg (1.20 mmol) 3-phenyl-3-[4-(3-trifluoromethyl-phenoxy)-phenoxy]-1-chloropropane, 184 mg (1.20 mmol) sarcosine ethyl ester hydrochloride, 0.416 mL (2.40 mmol) diisopropylethylamine, and 6 mL dry N-methylpyrrolidinone. The reaction was heated at 90-95° C. for 60 h, cooled, and poured into water. After extracting with ethyl acetate, the organic layer was washed with water (3 times) and brine, dried over sodium sulfate, and evaporated. The residue was chromatographed on silica gel using methylene chloride/methanol as eluant to afford 250 mg (43%) of an oil.

Workup

  1. customTo a 125 mL round-bottomed flask equipped with condenser and nitrogen inlet
  2. temperaturecooled
  3. extractionAfter extracting with ethyl acetate
  4. washthe organic layer was washed with water (3 times) and brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-9710c24986b741fdb39be5849545c0ab
Source dataset
uspto-grants-2003_05
Patent number
US06566550B2

Reaction notes

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