Sodium hydride → HCID 86741682, compound

HRID 2119136Notes

Reaction equation

HRID 2119136 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([SH:8])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].Br[C:12]1[CH:17]=[CH:16][C:15]([C@H:18]2[N:26]3[C@@H:21]([CH2:22][CH2:23][CH2:24][CH2:25]3)[CH2:20][CH2:19]2)=[CH:14][CH:13]=1>CN(C=O)C>[CH2:20]1[C@H:21]2[N:26]([CH2:25][CH2:24][CH2:23][CH2:22]2)[C@H:18]([C:15]2[CH:14]=[CH:13][C:12]([S:8][C:4]3[CH:3]=[C:2]([NH2:1])[CH:7]=[CH:6][CH:5]=3)=[CH:17][CH:16]=2)[CH2:19]1

Participants

5

Reactant 3

HCID 24758Sodium hydride2×HCID 315773-AminothiophenolHCID 13606121HCID 13606121, compound

Product 1

HCID 86741682HCID 86741682, compoundYield 46.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 2 g (0.016 mole) of 3-aminothiophenol in 25 mL of dry DMF was added to 0.016 mole of sodium hydride (from 0.77 g of 50% sodium hydride washed with hexane to remove the oil). After all the sodium hydride has reacted, a solution of 2.8 g (0.01 mole) of trans-3-(4-bromophenyl)octahydroindolizine in 20 ml of dry DMF and 0.72 g (0.005 mole) of cuprous oxide were added. The mixture was refluxed overnight. Then an additional 0.35 g (0.002 mole) of cuprous oxide was added to the reaction mixture, and the mixture was refluxed for two days. The reaction was the cooled to room temperature, filtered and the DMF evaporated in vacuo to give a brown oil. The oil was flash chromatographed in SiO2 using 75% hexane, 25% EtOAc as the eluant. The product bearing fractions were pooled and the solvent evacuated in vacuo to give 1.5 g (46% yield) of the title compound as a red oil.

Workup

  1. washwashed with hexane
  2. customto remove the oil)
  3. customAfter all the sodium hydride has reacted
  4. temperatureThe mixture was refluxed overnight
  5. temperaturethe mixture was refluxed for two days
  6. filtrationfiltered
  7. customthe DMF evaporated in vacuo
  8. customto give a brown oil
  9. customchromatographed in SiO2 using 75% hexane
  10. customthe solvent evacuated in vacuo

Sources & evidence

ORD record
ord-e3e0468a0fee41c0884429eb444e5d78
Source dataset
uspto-grants-1987_07
Patent number
US04683239

Reaction notes

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