3-{[(2E)-2-(1-Azabicyclo[2.2.2]oct-3-ylidene)-2-fluoroethyl]oxy}-9H-carbazole → 2-{[(2E)-2-(1-Azabicyclo[2.2.2]oct-3-ylidene)-2-fluoroethyl]oxy}-9H-carbazole

HRID 355427Notes

Reaction equation

HRID 355427 reaction equation
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][C:2]=1[O:14][CH2:15]/[C:16](=[C:18]1\[CH2:19][N:20]2[CH2:25][CH2:24][CH:23]\1[CH2:22][CH2:21]2)/[F:17].C(O)C.[ClH:29]>C(O)C>[ClH:29].[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][C:2]=1[O:14][CH2:15]/[C:16](=[C:18]1\[CH2:19][N:20]2[CH2:25][CH2:24][CH:23]\1[CH2:22][CH2:21]2)/[F:17]

Participants

4

Reactant 2

HCID 158589553-{[(2E)-2-(1-Azabicyclo[2.2.2]oct-3-ylidene)-2-fluoroethyl]oxy}-9H-carbazoleHCID 21887872Ethanol hydrochloride

Product 1

HCID 601962932-{[(2E)-2-(1-Azabicyclo[2.2.2]oct-3-ylidene)-2-fluoroethyl]oxy}-9H-carbazoleYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

After dissolving (E)-3-[2-(carbazol-2-yloxy)-1-fluoroethylidene]quinuclidine (95.5 g, 284 mmol) in ethanol (7.0 l) while heating under reflux, a hydrogen chloride ethanol solution (about 5M, 90 ml) was added to the resulting solution with ice-cooling, spending 3 minutes. After additional 0.5 hour of ice-cooling, the thus precipitated crystals were collected by filtration and dried to give the title compound (85.2 g, 228 mmol, 80%).

Workup

  1. temperaturewhile heating
  2. temperatureunder reflux
  3. temperaturecooling
  4. temperatureAfter additional 0.5 hour of ice-cooling
  5. filtrationthe thus precipitated crystals were collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-a8ffb67604b74b15a726a3fb7f39f937
Source dataset
uspto-grants-1998_11
Patent number
US05830902

Reaction notes

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