N,N-Diethyl-6-diphenylmethyl-5,5-ethylenedioxy-1-azabicyclo-[2.2.2]octane-3-carboxamide → HCID 131720990, compound

HRID 1458894Notes

Reaction equation

HRID 1458894 reaction equation
C([N:3](CC)[C:4]([CH:6]1[CH:11]2[CH2:12][CH2:13][N:8]([CH:9](C(C3C=CC=CC=3)C3C=CC=CC=3)[C:10]32[O:17][CH2:16][CH2:15][O:14]3)[CH2:7]1)=[O:5])C>C[O-].[Na+]>[CH2:15]1[CH2:16][O:17][C:10]2([CH2:9][N:8]3[CH2:13][CH2:12][CH:11]2[CH:6]([C:4]([NH2:3])=[O:5])[CH2:7]3)[O:14]1

Participants

3

Reactant 1

HCID 53633468N,N-Diethyl-6-diphenylmethyl-5,5-ethylenedioxy-1-azabicyclo-[2.2.2]octane-3-carboxamide

Product 1

HCID 131720990HCID 131720990, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 10942334Sodium MethoxideSolvent

Procedure

A suspension of 21 (9.8 g, 22 mmol) in sodium methoxide (28% in MeOH; 400 g) was heated at reflux temperature for 9 hours. The resulting solution was poured on ice (300 ml) and extracted with CH2Cl2 (150 ml) three times. The combined extracts were dried over sodium sulfate (Na2SO4) and concentrated. The clude was purified by recrystallization from ethanol (EtOH) to give 22 (1:4 mixture at 6-position ; 8.4 9, 19 mmol, 87%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 9 hours
  3. additionThe resulting solution was poured on ice (300 ml)
  4. extractionextracted with CH2Cl2 (150 ml) three times
  5. dry with materialThe combined extracts were dried over sodium sulfate (Na2SO4)
  6. concentrationconcentrated
  7. customThe clude was purified by recrystallization from ethanol (EtOH)

Sources & evidence

ORD record
ord-0d7bbddd8420494d8a3585512e757c26
Source dataset
uspto-grants-1998_12
Patent number
US05852038

Reaction notes

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