Ethyl Bromide → HCID 20308062, compound

HRID 1287287Notes

Reaction equation

HRID 1287287 reaction equation
[NH2:1][CH:2]1[CH:14]2[CH:6]([CH2:7][C:8]3[C:13]2=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH2:5][CH2:4][CH2:3]1.C([O-])([O-])=O.[K+].[K+].[CH2:21](Br)[CH3:22].[CH2:24](C(C)=O)[CH3:25]>>[CH2:24]([N:1]([CH2:21][CH3:22])[CH:2]1[CH:14]2[CH:6]([CH2:7][C:8]3[C:13]2=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH2:5][CH2:4][CH2:3]1)[CH3:25]

Participants

5

Reactant 4

HCID 6332Ethyl BromideHCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 20308065HCID 20308065, compound

Product 1

HCID 20308062HCID 20308062, compound

Procedure

The above amine is added to a suspension of 40 g of K2CO3 in 200 ml of methyl ethyl ketone and stirred while 22 g of ethyl bromide is added slowly over 2 hrs. The mixture is then heated under reflux for 5 hrs., cooled and filtered. Solvent is removed from the filtrate and the residue mixed with water and CHCl3. The organic layer is dried and freed of solvent to leave about 15 g of N,N-diethyl-4-amino-1,2,3,4,4a,9a-hexahydrofluorene which is subjected to a Birch reduction as per Example 1E to give N,N-diethyl-4-amino-1,2,3,4,5,8,4a,9a-octahydrofluorene which is reacted with hydrogen peroxide in the presence of formic acid as per Example 1 F to form the title compound.

Workup

  1. additionis added slowly over 2 hrs
  2. temperatureThe mixture is then heated
  3. temperatureunder reflux for 5 hrs
  4. temperature, cooled
  5. filtrationfiltered
  6. customSolvent is removed from the filtrate
  7. additionthe residue mixed with water and CHCl3
  8. customThe organic layer is dried

Sources & evidence

ORD record
ord-9375ee2527e7488a839759ccc228254c
Source dataset
uspto-grants-1976_10
Patent number
US03984419

Reaction notes

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