Dichloromethane → HCID 131715046, compound

HRID 980812Notes

Reaction equation

HRID 980812 reaction equation
[OH-:1].[K+].[N:3]1([CH2:9][CH:10]2[C:13]3=[CH:14][CH:15]=[CH:16][CH:17]=[C:12]3[CH2:11]2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[Br:18][CH2:19][CH2:20][CH2:21]Br.[CH2:23](Cl)Cl>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC>[Br:18][CH2:19][CH2:20][CH2:21][O:1][C:15]1[CH:14]=[C:13]2[CH:10]([CH2:9][N:3]3[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]3)[CH:11]([CH3:23])[C:12]2=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 6344Dichloromethane2×HCID 80011,3-DibromopropaneHCID 14797Potassium HydroxideHCID 131715047HCID 131715047, compound

Product 1

HCID 131715046HCID 131715046, compound

Reagents, catalysts & solvents 1

HCID 70681Tetrabutylammonium ChlorideCatalyst

Procedure

Aqueous potassium hydroxide (45%) is added to a stirred solution of the hydrochloride salt of the piperidinylmethylbenzocyclobutene obtained in the preceding step (6.5 g) in methylene chloride (30 ml) under nitrogen. The solution is stirred at RT for 30 minutes, and tetrabutylammonium chloride (0.9 g) and 1,3-dibromopropane (26 ml) are added to the stirred reaction mixture. The reaction mixture is stirred for an additional 2.5 hours, diluted with methylene chloride, washed with water, and extracted with 5% aqueous HCl. The acidic extract is washed with ether and basified affording a cloudy solution, which is extracted with methylene chloride. The organic extract is washed with sat'd NaCl solution, dried, filtered and evaporated in vacuo affording the desired product as an oil.

Workup

  1. stirringThe reaction mixture is stirred for an additional 2.5 hours
  2. washwashed with water
  3. extractionextracted with 5% aqueous HCl
  4. extractionThe acidic extract
  5. washis washed with ether
  6. custombasified affording a cloudy solution, which
  7. extractionis extracted with methylene chloride
  8. extractionThe organic extract
  9. washis washed with sat'd NaCl solution
  10. customdried
  11. filtrationfiltered
  12. customevaporated in vacuo

Sources & evidence

ORD record
ord-ab2b879ffce64d26b347c0f0a124b7de
Source dataset
uspto-grants-1987_01
Patent number
US04639442

Reaction notes

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