Potassium Hydroxide → HCID 20339677, compound

HRID 1395432Notes

Reaction equation

HRID 1395432 reaction equation
[ClH:1].[C:2]1([C:8]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:9][CH:10]2[C:15](=O)[CH:14]3[CH2:17][CH2:18][N:11]2[CH2:12][CH2:13]3)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.NN.O.[OH-].[K+]>C(O)COCCO>[ClH:1].[C:25]1([C:8]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:9][CH:10]2[CH2:15][CH:14]3[CH2:17][CH2:18][N:11]2[CH2:12][CH2:13]3)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 14797Potassium Hydroxide2×HCID 24654Hydrazine hydrate (1:1)HCID 86736990HCID 86736990, compound

Product 1

HCID 20339677HCID 20339677, compound

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

Procedure

A mixture of 2.25 grams (5.38 mmol) of 2-(2,2,2-triphenylethyl)-1-azabicyclo[2.2.2]octane-3-one hydrochloride (XI), 1.14 grams (19.4 mmol) 85% H2NNH2.H2O, 1.5 grams (23 mmol) 85% KOH and 160 ml of diethylene glycol is heated to reflux for 2 hours. The resultant solution is cooled to room temperature and poured into 1.0 liter of ice-water. The aqueous layer has a pH of about 12.0 which is adjusted to about 14.0 with aqueous KOH. The solution is extracted twice with diethyl ether, and the combined ether extracts are shaken with dilute HCl (400 ml. containing 4 ml. of concentrated HCl) resulting in the formation of a fine solid precipitate. The precipitate is filtered and washed with water and diethyl-ether, and air-dried to provide 892 mg. of a white powder. The white powder is recrystallized from methanolether and dried in vacuo (0.1 mm. Hg) at 100° for 18 hours and then at 140° for 2 hours to provide the product, 2-(2,2,2-triphenylethyl)-1-azabicyclo[2.2.2]octane hydrochloride (VIII); MW:403.99.

Workup

  1. temperatureis heated
  2. temperatureto reflux for 2 hours
  3. extractionThe solution is extracted twice with diethyl ether
  4. customresulting in the formation of a fine solid precipitate
  5. filtrationThe precipitate is filtered
  6. washwashed with water and diethyl-ether
  7. customair-dried
  8. customto provide 892 mg
  9. customThe white powder is recrystallized from methanolether
  10. customdried in vacuo (0.1 mm. Hg) at 100° for 18 hours

Sources & evidence

ORD record
ord-6c356a435b1b4260bcc84d14556d78b6
Source dataset
uspto-grants-1980_05
Patent number
US04203990

Reaction notes

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