Iodine → HCID 20077842, compound

HRID 1654440Notes

Reaction equation

HRID 1654440 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mg].II.[CH2:11]([N:18]1[CH2:23][CH2:22][N:21]([C:24]2([C:30]#N)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[CH2:20][CH2:19]1)C1C=CC=CC=1>O1CCCC1.BrCCBr>[CH2:11]([N:18]1[CH2:19][CH2:20][N:21]([C:24]2([C:30]3[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=3)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]2)[CH2:22][CH2:23]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 807IodineHCID 7961BromobenzeneHCID 5462224MagnesiumHCID 22314793HCID 22314793, compound

Product 1

HCID 20077842HCID 20077842, compound

Reagents, catalysts & solvents 2

HCID 78391,2-DibromoethaneCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To bromobenzene (0.6 g) and magnesium turnings (0.2 g) in 30 mL dry tetrahydrofuran under nitrogen was added a small crystal of iodine and 10 drops of 1,2-dibromoethane. After small bubbles began to form, the reaction was stirred and heated to reflux for 4 hours. After cooling to room temperature, 1-benzyl-4-(1-cyanocyclohexyl)piperazine (1 g) was added. After 23 hours, the reaction was filtered, 20 mL saturated aqueous ammonium chloride was added and the mixture was extracted with diethyl ether. The ether was dried and removed in vacuo. The residue was chromatographed on silica gel eluted with chloroform to yield pure 1-benzyl-4-(1-phenylcyclohexyl)piperazine.

Workup

  1. customto form
  2. temperatureheated
  3. temperatureto reflux for 4 hours
  4. filtrationthe reaction was filtered
  5. addition20 mL saturated aqueous ammonium chloride was added
  6. extractionthe mixture was extracted with diethyl ether
  7. dry with materialThe ether was dried
  8. customremoved in vacuo
  9. customThe residue was chromatographed on silica gel
  10. washeluted with chloroform

Sources & evidence

ORD record
ord-dfcacfdcf8a74492bbbe0b9129b89fd2
Source dataset
uspto-grants-1995_04
Patent number
US05407834

Reaction notes

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