1-Fluoro-2-nitrobenzene → 8-Benzyl-N-(2-nitrophenyl)-8-azabicyclo[3.2.1]octan-3-amine

HRID 1992046Notes

Reaction equation

HRID 1992046 reaction equation
[CH2:1]([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][CH:11]([NH2:16])[CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.F[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[N+:33]([O-:35])=[O:34]>CN1C(=O)CCC1.CCOC(C)=O>[CH2:1]([N:8]1[CH:9]2[CH2:15][CH2:14][CH:13]1[CH2:12][CH:11]([NH:16][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[N+:33]([O-:35])=[O:34])[CH2:10]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 738951-Fluoro-2-nitrobenzeneHCID 81531DiisopropylethylamineHCID 128321038-Benzyl-8-azabicyclo(3.2.1)octan-3-amine

Product 1

HCID 185070268-Benzyl-N-(2-nitrophenyl)-8-azabicyclo[3.2.1]octan-3-amineYield 31.1%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

5.62 g (27.82 mmol) 8-benzyl-8-azabicyclo[3.2.1]octan-3-amine (u17094-94) and 9.7 ml (55.46 mmoml) of Hunig's base were dissolved in 200 ml NMP. 4.32 g (30.60 mmol) 1-fluoro-2-nitrobenzene was then added and the mixture was stirred at RT for 3 hrs. The reaction mixture was diluted with EtOAc and washed with water and dried over sodium sulfate. The solvent was removed partially under reduced pressure and was left in refrigerator overnight. The solid was filtered off to afford 2.92 g of product as a yellow powder. The solvent was removed from filtration to give additional 5.7 g of product as an orange-yellow residue.

Workup

  1. washwashed with water
  2. dry with materialdried over sodium sulfate
  3. customThe solvent was removed partially under reduced pressure
  4. waitwas left in refrigerator overnight
  5. filtrationThe solid was filtered off

Sources & evidence

ORD record
ord-05b846e7297742f39ca0abff504cb597
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

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