Sodium Iodide → HCID 86616267, compound

HRID 2240113Notes

Reaction equation

HRID 2240113 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]3[N:15]=[C:16]([CH2:23][CH2:24][CH2:25][NH2:26])[C:17]4[S:22][CH2:21][CH2:20][C:18]=4[N:19]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[I-:27].[Na+].CN(C)[C@@H]1CCCC[C@H]1N>O1CCOCC1.[Cu](I)I>[I:27][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]3[N:15]=[C:16]([CH2:23][CH2:24][CH2:25][NH2:26])[C:17]4[S:22][CH2:21][CH2:20][C:18]=4[N:19]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 11275066(1R,2R)-N1,N1-Dimethylcyclohexane-1,2-diamineHCID 86616268HCID 86616268, compound

Product 1

HCID 86616267HCID 86616267, compoundYield 98.1%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
140 °C

Procedure

1.55 g (3.6 mmol) of {2-[4-(4-bromophenyl)piperazin-1-yl]-6,7-dihydrothieno[3,2-d]pyrimidin-4-yl}propylamine (VII), 1.1 g (7.2 mmol) of sodium iodide, and 0.036 g (0.19 mmol) of copper iodide are taken, and under an argon atmosphere 0.060 mL (0.38 mmol) of trans-N,N-dimethyl-1,2-cyclohexanediamine and 7 mL of anhydrous/degassed dioxane are added. The reaction mixture is heated for 1.5 hours at 140° C. in the microwave, then diluted with dioxane, and suction filtered through Alox. The dioxane was concentrated by evaporation. 1.70 g of product VIII (81%) is obtained as a powder.

Workup

  1. filtrationfiltered through Alox
  2. concentrationThe dioxane was concentrated by evaporation

Sources & evidence

ORD record
ord-4e9cb3c1959441ff9e4c032a1a48265a
Source dataset
uspto-grants-2010_05
Patent number
US07723341B2

Reaction notes

Loading…