Water → HCID 19878335, compound

HRID 1885914Notes

Reaction equation

HRID 1885914 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]4[CH:24]=[CH:23][CH:22]=[CH:21][C:19]4=3)[C:14]3[C:9]2=[CH:10][C:11]([O:25][CH3:26])=[CH:12][CH:13]=3)=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:30][CH2:31][N:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1.O>CN(C)C=O>[CH3:26][O:25][C:11]1[CH:10]=[C:9]2[C:14]([C:15]3[C:20]([CH:8]2[C:5]2[CH:4]=[CH:3][C:2]([O:1][CH2:30][CH2:31][N:32]4[CH2:36][CH2:35][CH2:34][CH2:33]4)=[CH:7][CH:6]=2)=[C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]2=[CH:17][CH:16]=3)=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 816691-(2-Chloroethyl)pyrrolidineHCID 19878336HCID 19878336, compound

Product 1

HCID 19878335HCID 19878335, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A 7 g portion of the compound of Example 1 was dissolved in 100 ml of dry dimethylformamide, and to it was added 1.05 g of 50% mineral oil dispersion of sodium hydride and 4 g of 1-(2-chloroethyl)pyrrolidine. The mixture was then stirred at 60° C. for 3 hours and cooled. It was then poured over 500 ml of ice and water, and the mixture was extracted 3 times with 250 ml portions of ethyl acetate. The organic extract was washed with two 50 ml portions of brine, dried and concentrated under vacuum. The residue was chromatographed over a 5 cm×50 cm silica gel column with 3:1 ethyl acetate:toluene, followed by ethyl acetate. The product-containing fractions were combined and concentrated under vacuum to contain 4.5 g of the title compound.

Workup

  1. temperaturecooled
  2. extractionthe mixture was extracted 3 times with 250 ml portions of ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with two 50 ml portions of brine
  5. customdried
  6. concentrationconcentrated under vacuum
  7. customThe residue was chromatographed over a 5 cm×50 cm silica gel column with 3:1 ethyl acetate
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-98017511eb824e3e8e4e335d1b253d3d
Source dataset
uspto-grants-1992_09
Patent number
US05147880

Reaction notes

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