Sodium Iodide → HCID 13018732, compound

HRID 26418Notes

Reaction equation

HRID 26418 reaction equation
[C:1]1([C:7]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[CH2:14][CH:13]3[C:8]=2[CH2:9][CH2:10][NH:11][CH2:12]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+].[CH:29](Br)([CH3:31])[CH3:30]>CN(C)C=O>[CH:29]([N:11]1[CH2:10][CH2:9][C:8]2[CH:13]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:7]=2[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:12]1)([CH3:31])[CH3:30]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 63582-BromopropaneHCID 10340Sodium CarbonateHCID 213233011,2,3,4,10,10a-Hexahydro-5phenylbenz[g]isoquinoline

Product 1

HCID 13018732HCID 13018732, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 22.0 g of 1,2,3,4,10,10a-hexahydro-5phenylbenz[g]isoquinoline, 20.0 g of sodium carbonate and 0.2 g of sodium iodide in 180 ml of dimethylformamide are preheated to 50°. 16.5 g of isopropylbromide in 50 ml of dimethylformamide are added dropwise to the suspension over a 2 hour period, the reaction mixture further stirred for 3.5 hours at the same temperature, cooled and poured onto ice/water. The organic substance is extracted with benzene, the extracts washed with water, dried over sodium sulphate and evaporated and the title compound which remains converted to the fumarate form in isopropyl. M.P. 199°-200°.

Workup

  1. customare preheated to 50°
  2. temperaturecooled
  3. additionpoured onto ice/water
  4. extractionThe organic substance is extracted with benzene
  5. washthe extracts washed with water
  6. dry with materialdried over sodium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-7ec1069a0b9b4c748bd600215aa1bbb0
Source dataset
uspto-grants-1979_04
Patent number
US04150136

Reaction notes

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