Aniline → HCID 3126467, compound

HRID 349211Notes

Reaction equation

HRID 349211 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[N:9]12[CH2:16][CH2:15][CH:12]([CH2:13][CH2:14]1)[C:11](=O)[CH2:10]2.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClC(Cl)C>[C:2]1([NH:1][CH:11]2[CH:12]3[CH2:15][CH2:16][N:9]([CH2:14][CH2:13]3)[CH2:10]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 1020191-Azabicyclo(2.2.2)octan-3-one, hydrochloride (1:1)HCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 3126467HCID 3126467, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

(Method 1A) To a mixture of 9.3 g (0.1 mol) of aniline and 16.1 g (0.1 mol) of 1-azabicyclo[2.2.2]octan-3-one hydrochloride in 250 mL of dichloroethane (DCE) was added 31.8 g (0.15 mol) of Na(OAc)3BH and the mixture was stirred overnight at room temperature. The reaction was quenched with 3 N NaOH. The layers were separated and the aqueous layer was extracted with an additional portion of CHCl3. The organic layers were combined, dried over NaSO4, and then filtered and the solvent was evaporated in vacuo. Th residue was chromatographed on silica (95/5 CHCl3/10% NH4OH in MeOH) to give N-Phenyl-1-azabicyclo[2.2.2]octan-3-amine (6.0 g 30%) as an off-white solid. MH+=203. 1H NMR (CDCl3) 1.46 (m, 1H), 1.75 (m, 3H), 2.0 (m, 1H), 2.55 (m, 1H), 2.95 (m, 4H), 3.4 (m, 2H), 3.8 (s, 1H), 6.6 (d, 2H), 6.75 (t, 1H), 7.2 (t, 2H).

Workup

  1. customThe reaction was quenched with 3 N NaOH
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with an additional portion of CHCl3
  4. dry with materialdried over NaSO4
  5. filtrationfiltered
  6. customthe solvent was evaporated in vacuo
  7. customTh residue was chromatographed on silica (95/5 CHCl3/10% NH4OH in MeOH)

Sources & evidence

ORD record
ord-f94ca5ddcb7e4aa3bf1e632704a3119a
Source dataset
uspto-grants-2007_02
Patent number
US07179818B2

Reaction notes

Loading…