Ammonia → HCID 21447123, compound

HRID 597230Notes

Reaction equation

HRID 597230 reaction equation
[NH3:1].C([Li])CCC.[C:7]1([C:13]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([CH2:18][CH:19]2[CH2:24][CH:23]3[CH2:25][CH2:26][N:20]2[CH2:21][CH2:22]3)[C:14]([O:16]C)=O)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(=O)=O>CCCCCC.O1CCCC1>[C:27]1([C:13]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)([CH2:18][CH:19]2[CH2:24][CH:23]3[CH2:25][CH2:26][N:20]2[CH2:21][CH2:22]3)[C:14]([NH2:1])=[O:16])[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 280Carbon DioxideHCID 20339672HCID 20339672, compoundHCID 178418339Butyllithium

Product 1

HCID 21447123HCID 21447123, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To a solution of 25 parts by volume liquid ammonia in 22 parts dry tetrahydrofuran is added dropwise over a 5 minute period 10 parts by volume of a 2.3 M solution of butyl lithium in hexane under reflux under a dry ice condenser. Then, a solution of 3.9 parts methyl 2,2-diphenyl-3-(1-azabicyclo[2.2.2]oct-2-yl)propionate in 18 parts dry tetrahydrofuran is added dropwise, with stirring. After stirring the resulting mixture under reflux for 3 hours the dry ice condenser is removed, and the mixture stirred at ambient temperature for a further two hours. The solvents are then removed in vacuo. The residual gum is suspended in water and extracted with a 1:1 ether-benzene solution. The ether-benzene extract is separated, washed with water, dried over anhydrous sodium sulfate and stripped in vacuo. The residue is triturated with 50 parts of n-pentane. The undissolved solid is filtered off, washed with n-pentane and air dried to give a white powder. This powder is recrystallized from a mixture of benzene and petroleum ether to afford, as white needles, 2,2-diphenyl-3-(1-azabicyclo[2.2.2]oct-2-yl)propionamide. This compound melts at about 192°-194° C. and is represented by the following structural formula. ##STR12##

Workup

  1. temperatureunder reflux under a dry ice condenser
  2. stirringAfter stirring the resulting mixture
  3. customis removed
  4. stirringthe mixture stirred at ambient temperature for a further two hours
  5. customThe solvents are then removed in vacuo
  6. extractionextracted with a 1:1 ether-benzene solution
  7. extractionThe ether-benzene extract
  8. customis separated
  9. washwashed with water
  10. dry with materialdried over anhydrous sodium sulfate
  11. customThe residue is triturated with 50 parts of n-pentane
  12. filtrationThe undissolved solid is filtered off
  13. washwashed with n-pentane and air
  14. customdried
  15. customto give a white powder
  16. customThis powder is recrystallized from a mixture of benzene and petroleum ether

Sources & evidence

ORD record
ord-8f3b763b4d9849da835fe6f608fb399f
Source dataset
uspto-grants-1977_03
Patent number
US04013667

Reaction notes

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