Cesium fluoride → HCID 19849428, compound

HRID 1607799Notes

Reaction equation

HRID 1607799 reaction equation
[F-:1].[Cs+].[CH2:3]([C:8]12[CH2:15][CH2:14][C:11]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[C:20]([N+]([O-])=O)[CH:19]=3)([CH2:12][CH2:13]1)[CH2:10][CH2:9]2)[CH2:4][CH2:5][CH2:6][CH3:7].C(C12CCC(CCC3C=CC(Br)=CC=3)(CC1)CC2)CCCC.[Cu](C#N)C#N>CN1CCCC1=O>[CH2:3]([C:8]12[CH2:15][CH2:14][C:11]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[C:20]([F:1])[CH:19]=3)([CH2:12][CH2:13]1)[CH2:10][CH2:9]2)[CH2:4][CH2:5][CH2:6][CH3:7]

Participants

6

Reactant 4

HCID 25953Cesium fluorideHCID 19849347HCID 19849347, compoundHCID 19849355HCID 19849355, compoundHCID 178418260HCID 178418260, compound

Product 1

HCID 19849428HCID 19849428, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

7.6 g of caesium fluoride are added to a mixture of 3.55 g of 1-[4-pentylbicyclo(2.2.2)octyl]-2-(4-cyano-3-nitrophenyl)ethane (obtainable by nitrating 1-[4-pentylbicyclo(2.2.2)octyl]-2-(4-bromophenyl)-ethane, reacting the product with copper cyanide in N-methylpyrrolidone and subsequently purifying the product by chromatography) and 25 ml of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone, and the mixture is heated at 120oC for 5 hours. Adding water and working up after extraction gives 1-[4-pentylbicyclo(2.2.2)octyl]-2-(4-cyano-3-fluorophenyl)-ethane.

Workup

  1. customsubsequently purifying the product by chromatography) and 25 ml of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone
  2. temperaturethe mixture is heated at 120oC for 5 hours
  3. extractionafter extraction

Sources & evidence

ORD record
ord-80b592e8fe364c8d901aadd8a1e3f2b2
Source dataset
uspto-grants-1989_09
Patent number
US04867904

Reaction notes

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