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1-Bromoheptane → 3-n-Heptyl-1-(4-nitrophenyl)-3-azabicyclo[3.1.1]heptane-2,4-dione

HRID 35094
Notes
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Reaction equation

HRID 35094 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([C:12]23[CH2:18][CH:16]([CH2:17]2)[C:15](=[O:19])[NH:14][C:13]3=[O:20])=[CH:8][CH:7]=1)([O-:5])=[O:4].[CH2:21](Br)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].C(OCC)(=O)C.CCCCCC>CN(C)C=O>[CH2:21]([N:14]1[C:15](=[O:19])[CH:16]2[CH2:17][C:12]([C:9]3[CH:8]=[CH:7][C:6]([N+:3]([O-:5])=[O:4])=[CH:11][CH:10]=3)([CH2:18]2)[C:13]1=[O:20])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 123691-BromoheptaneHCID 24758Sodium hydrideHCID 148726291-(4-Nitrophenyl)-3-azabicyclo[3.1.1]heptane-2,4-dioneHCID 21226206Ethyl acetate hexane

Product 1

HCID 148726323-n-Heptyl-1-(4-nitrophenyl)-3-azabicyclo[3.1.1]heptane-2,4-dione

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent
3×

Procedure

0.36 g of sodium hydride is added to a solution of 2.46 g of 1-(4-nitrophenyl)-3-azabicyclo[3.1.1]heptane-2,4-dione in 25 ml of N,N-dimethylformamide and the whole is stirred at room temperature for 30 minutes. 2.68g of n-heptyl bromide dissolved in 10 ml of N,N-dimethylformamide are then added dropwise thereto. When the reaction is complete, the reaction mixture is freed of N,N-dimethylformamide. The residue is partitioned between ethyl acetate and water, and the organic phase is dried over magnesium sulphate. After concentration by evaporation and purification by chromatography over silica gel in the system ethyl acetate/hexane 2:5, the product is obtained in the form of a solid. Melting point 91°-92°. Rf (ethyl acetate/hexane 4:1)=0.63.

Workup

  1. additionare then added dropwise
  2. customThe residue is partitioned between ethyl acetate and water
  3. dry with materialthe organic phase is dried over magnesium sulphate
  4. concentrationAfter concentration
  5. customby evaporation and purification by chromatography over silica gel in the system ethyl acetate/hexane 2:5
  6. customthe product is obtained in the form of a solid

Sources & evidence

ORD record
ord-33e11a100eb14ea091b496fad4c0cc32
Source dataset
uspto-grants-1988_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04764640

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes