Sodium Azide → HCID 19887602, compound

HRID 654525Notes

Reaction equation

HRID 654525 reaction equation
Br.Br[CH2:3][C:4]([C:6]12[CH2:13][N:10]([CH2:11][CH2:12]1)[CH2:9][CH2:8][CH2:7]2)=[O:5].[N-:14]=[N+:15]=[N-:16].[Na+]>CN(C)C=O>[N:14]([CH2:3][C:4]([C:6]12[CH2:13][N:10]([CH2:11][CH2:12]1)[CH2:9][CH2:8][CH2:7]2)=[O:5])=[N+:15]=[N-:16]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 19809490HCID 19809490, compound

Product 1

HCID 19887602HCID 19887602, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-(α-bromoacetyl)-1-azabicyclo[3.2.1]octane hydrobromide (D27) (1.8 g; 5.8 mmole) in dry N,N-dimethylformamide (25 ml) was treated with sodium azide (0.41 g; 6.3 mmole) and stirred in the dark at room temperature for 21h. The reaction mixture was concentrated in vacuo and the residue was treated with a saturated potassium carbonate solution (25 ml) and extracted into chloroform (4×25 ml). The dried (sodium sulphate) organic layers were concentrated in vacuo to give the title compound (D28) as an orange oil (0.75 g; 67%) which was used in the next stage without purification.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionthe residue was treated with a saturated potassium carbonate solution (25 ml)
  3. extractionextracted into chloroform (4×25 ml)
  4. dry with materialThe dried (sodium sulphate) organic layers
  5. concentrationwere concentrated in vacuo

Sources & evidence

ORD record
ord-0cc1e144ced741e6beea38efe3dc1061
Source dataset
uspto-grants-1992_07
Patent number
US05132316

Reaction notes

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