Water → HCID 23311345, compound

HRID 746049Notes

Reaction equation

HRID 746049 reaction equation
[C:1]1([C:7]2([CH2:16][CH2:17][NH:18][CH3:19])[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[O:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:20]1([CH2:23]Cl)[CH2:22][CH2:21]1.[C:25]([O-:28])([O-:27])=O.[K+].[K+].[OH2:31]>CN(C=O)C>[C:8]([OH:31])(=[O:9])/[CH:7]=[CH:16]/[C:25]([OH:28])=[O:27].[C:1]1([C:7]2([CH2:16][CH2:17][N:18]([CH2:23][CH:20]3[CH2:22][CH2:21]3)[CH3:19])[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[O:9][CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 80013(Chloromethyl)cyclopropaneHCID 13656118HCID 13656118, compound

Product 1

HCID 23311345HCID 23311345, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4.0 g (15.8 mmole) of 2-(3-phenyl-2,3-dihydrobenzofuran-3-yl)-N-methylethylamine, 1.54 g (17.1 mmole) cyclopropylmethyl chloride, 6.9 g (50.0 mmole) K2CO3 and 0.2 g KI in 40 ml DMF was warmed to 65° and maintained there for 4 hours. After cooling, the reaction mixture was poured into 400 ml water and extracted with Et2O (3×200 ml). The combined organics were washed with saturated NaCl solution and dried over Na2SO4. After filtration, the solution was stirred with several grams of silica gel and decanted. After adding 1.85 g fumaric acid and stirring for 1 hour, 4.2 g of solid was collected. This material was recrystallized from CH3CN to give 2.2 g (33%) of crystals, m.p. 154°-156°.

Workup

  1. temperaturewas warmed to 65°
  2. temperaturemaintained there for 4 hours
  3. temperatureAfter cooling
  4. extractionextracted with Et2O (3×200 ml)
  5. washThe combined organics were washed with saturated NaCl solution
  6. dry with materialdried over Na2SO4
  7. filtrationAfter filtration
  8. customdecanted
  9. additionAfter adding 1.85 g fumaric acid
  10. stirringstirring for 1 hour
  11. custom4.2 g of solid was collected
  12. customThis material was recrystallized from CH3CN

Sources & evidence

ORD record
ord-7e68972410be4b87932a527fd807a630
Source dataset
uspto-grants-1986_07
Patent number
US04602035

Reaction notes

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