Aniline → HCID 3126467, compound

HRID 349212Notes

Reaction equation

HRID 349212 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C:3](=O)[CH2:2]2.[NH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[BH4-].[Na+]>CCO>[C:11]1([NH:10][CH:3]2[CH:4]3[CH2:7][CH2:8][N:1]([CH2:6][CH2:5]3)[CH2:2]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 195073-QuinuclidinoneHCID 4311764Sodium borohydride

Product 1

HCID 3126467HCID 3126467, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(Method 1B) A mixture of 1.26 g of 1-azabicyclo[2.2.2]octan-3-one and 0.93 g of aniline and 4.4 mL of Ti(/PrO)4 was stirred overnight at room temperature. The reaction mixture was diluted with EtOH and then NaBH4 pellets (0.8 g) were added until reaction was judged complete by TLC. The solvent was evaporated in vacuo. The residue was diluted with 3N NaOH, water and EtOAc and the mixture was filtered through dicalite. The filter pad was washed with additional EtOAc. The filtrate was transferred to a separatory funnel and the aqueous layer was extracted with an additional portion of EtOAc. The combined organic extracts were washed with water and then brine and then dried over K2CO3. The solution was filtered and the solvent was evaporated in vacuo. The residue was chromatographed on silica (90/7.5/2.5 CHCl3/MeOH/7.0 M NH3 in MeOH) to give N-Phenyl-1-azabicyclo[2.2.2]octan-3-amine (1.5 g, 75%) as a white solid. 1H NMR (CDCl3) is consistent with the one from Method 1A.

Workup

  1. customThe solvent was evaporated in vacuo
  2. additionThe residue was diluted with 3N NaOH, water and EtOAc
  3. filtrationthe mixture was filtered through dicalite
  4. washThe filter pad was washed with additional EtOAc
  5. customThe filtrate was transferred to a separatory funnel
  6. extractionthe aqueous layer was extracted with an additional portion of EtOAc
  7. washThe combined organic extracts were washed with water
  8. dry with materialbrine and then dried over K2CO3
  9. filtrationThe solution was filtered
  10. customthe solvent was evaporated in vacuo
  11. customThe residue was chromatographed on silica (90/7.5/2.5 CHCl3/MeOH/7.0 M NH3 in MeOH)

Sources & evidence

ORD record
ord-ea5d9c955af946a89b275a599e2bea34
Source dataset
uspto-grants-2007_02
Patent number
US07179818B2

Reaction notes

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