Ammonia → HCID 178444270, compound

HRID 1742789Notes

Reaction equation

HRID 1742789 reaction equation
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([CH:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][C:21](Br)=[CH:20][CH:19]=3)=[CH:14][CH2:13]2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].N.[CH3:26][N:27](C)C=O>>[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([CH:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][C:21]([C:26]#[N:27])=[CH:20][CH:19]=3)=[CH:14][CH2:13]2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 6228DimethylformamideHCID 178444248HCID 178444248, compound

Product 1

HCID 178444270HCID 178444270, compound

Procedure

In 20 ml of N,N-dimethylformamide, 7 g of the 1-(trans-4-pentylcyclohexyl)-4-(4-bromophenyl)dihydrobenzene, which had been obtained in Example 18, were dissolved, followed by the addition of 2.0 g of cuprous cyanide. The resulting mixture was reacted for 6 hours at reflux temperature. After the completion of the reaction, aqueous ammonia was added to the reaction mixture, followed by extraction with toluene. The extract was washed with aqueous ammonia and then with saturated NaCl. Anhydrous sodium sulfate was thereafter added to dry the extract. The toluene was distilled off under reduced pressure. The reaction product so obtained was recrystallized from ethanol, whereby 0.7 g of 1-(trans-4-pentylcyclohexyl)-4-(4-cyanophenyl)dihydrobenzene was obtained.

Workup

  1. dissolutionwere dissolved
  2. customThe resulting mixture was reacted for 6 hours
  3. temperatureat reflux temperature
  4. additionwas added to the reaction mixture
  5. extractionfollowed by extraction with toluene
  6. washThe extract was washed with aqueous ammonia
  7. additionAnhydrous sodium sulfate was thereafter added
  8. customto dry the extract
  9. distillationThe toluene was distilled off under reduced pressure
  10. customThe reaction product so obtained
  11. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-8f19b6f88f274b3db55d58b5b2936c22
Source dataset
uspto-grants-1994_08
Patent number
US05342546

Reaction notes

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