Dichloromethane → HCID 19838453, compound

HRID 1607140Notes

Reaction equation

HRID 1607140 reaction equation
[NH2:1][CH:2]1[CH2:14][C:13]2[C:5](=[CH:6][C:7]3[CH2:11][CH2:10][O:9][C:8]=3[CH:12]=2)[CH2:4][CH2:3]1.[OH-].[Na+].[CH2:17](Br)[CH:18]=[CH2:19].C(Cl)[Cl:22]>CO.C(#N)C>[ClH:22].[CH2:19]([NH:1][CH:2]1[CH2:14][C:13]2[C:5](=[CH:6][C:7]3[CH2:11][CH2:10][O:9][C:8]=3[CH:12]=2)[CH2:4][CH2:3]1)[CH:18]=[CH2:17]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 7841Allyl bromideHCID 14798Sodium HydroxideHCID 14234814HCID 14234814, compound

Product 1

HCID 19838453HCID 19838453, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

5.2 g of 7-amino-2,3,5,6,7,8-hexahydronaphtho[2,3-b]furan dissolved in 27.6 ml of methylene chloride are stirred at room temperature in the presence of 8.3 ml of 40% strength sodium hydroxide, 3.3 g of allyl bromide and 1 ml of 40% strength Triton B in methanol. After 20 hours' stirring, 1 ml of Triton B is added again, followed by a further 2 ml after 24 hours' stirring. After 96 hours' stirring, the mixture is separated off after being left to settle and evaporated under vacuum. The residue, taken up in ethyl ether, is washed with water and then dried over anhydrous sodium sulfate. After evaporation, 4.6 g of base are obtained. The corresponding hydrochloride is obtained in acetonitrile by adding a stoichiometric quantity of ethereal hydrogen chloride, and then recrystallized in water.

Workup

  1. addition1 ml of Triton B is added again
  2. waitfollowed by a further 2 ml after 24 hours
  3. stirring' stirring
  4. stirringAfter 96 hours' stirring
  5. customthe mixture is separated off
  6. waitafter being left
  7. customevaporated under vacuum
  8. washis washed with water
  9. dry with materialdried over anhydrous sodium sulfate
  10. customAfter evaporation, 4.6 g of base
  11. customare obtained

Sources & evidence

ORD record
ord-31bfadaf1198446f807c979ba214bf58
Source dataset
uspto-grants-1989_09
Patent number
US04863951

Reaction notes

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