Sodium Carbonate → HCID 20468410, compound

HRID 1903272Notes

Reaction equation

HRID 1903272 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]23[CH2:13][CH:12]2[CH2:11][NH:10][CH2:9]3)=[CH:4][CH:3]=1.Br[CH:15]([CH3:25])[C:16]([NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:17].C(=O)([O-])[O-].[Na+].[Na+].[OH-].[Na+]>O.C1(C)C=CC=CC=1>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]23[CH2:13][CH:12]2[CH2:11][N:10]([CH:15]([CH3:25])[C:16]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:17])[CH2:9]3)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 991132-Bromo-N-phenylpropanamideHCID 101303311-(4-Chlorophenyl)-3-azabicyclo[3.1.0]hexane

Product 1

HCID 20468410HCID 20468410, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 3.5 g. of (-)-1-(p-chlorophenyl)-3-azabicyclo[3.1.0]hexane (U.S. Pat. No. 4,131,611), 4.6 g. of 2-bromopropionanilide, 3.7 g. of sodium carbonate and 75 ml. of toluene is stirred and refluxed overnight. The mixture is diluted with 25 ml. of water and 5 ml. of 5 N sodium hydroxide and mixed. The alkaline aqueous layer is extracted with toluene. The toluene layers are combined, washed with water, dried, filtered and concentrated to an oil. The oil is triturated in 50 ml. of ether and filtered. The filtrate is acidified with 6 ml. of 3.55 N alcoholic hydrogen chloride and scratched and resuspended in ether repeatedly until crystalline. The solid is collected, washed with ether, dried, heated to solution in 25 ml. of acetonitrile, filtered and cooled, giving 1.2 g. of the desired product, m.p. 227°-228° C.

Workup

  1. additionA mixture of 3.5 g
  2. temperaturerefluxed overnight
  3. additionThe mixture is diluted with 25 ml
  4. extractionThe alkaline aqueous layer is extracted with toluene
  5. washwashed with water
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated to an oil
  9. customThe oil is triturated in 50 ml
  10. filtrationof ether and filtered
  11. customThe solid is collected
  12. washwashed with ether
  13. customdried
  14. temperatureheated to solution in 25 ml
  15. filtrationof acetonitrile, filtered
  16. temperaturecooled
  17. customgiving 1.2 g

Sources & evidence

ORD record
ord-d31b1b7320ff481aa21bd90b5328b37f
Source dataset
uspto-grants-1984_03
Patent number
US04435419

Reaction notes

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