Sodium Azide → HCID 58339729, compound

HRID 1505649Notes

Reaction equation

HRID 1505649 reaction equation
[CH2:1]([N:8]1[CH2:14][CH2:13][CH:12]2[CH:10]([O:11]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:15]=[N+:16]=[N-:17].[Na+].Cl([O-])(=O)(=O)=O.[Li+]>>[N:15]([C@@H:12]1[CH2:13][CH2:14][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:9][C@H:10]1[OH:11])=[N+:16]=[N-:17]

Participants

4

Reactant 3

HCID 33557Sodium AzideHCID 64214963-(Phenylmethyl)-7-oxa-3-azabicyclo[4.1.0]heptaneHCID 23665649Lithium perchlorate

Product 1

HCID 58339729HCID 58339729, compoundYield 67%

Procedure

A solution of 1.2 g of 3-benzyl-7-oxa-3-azabicyclo[4.1.0]heptane (6.3 mmol) was refluxed in the presence of 0.62 g of sodium azide (9.5 mmol) and 3 g of lithium perchlorate (19 mmol) for 4 hs. After completion reaction mixture was evaporated and the residue was extracted with dichloromethane, washed with water and combined organic fractions were dried over sodium sulfate and concentrated. The residue was purified on silica gel column using hexane-ethyl acetate 4:1 as eluent affording 980 mg of trans-4-azido-1-benzylpiperidin-3-ol.

Workup

  1. customAfter completion reaction mixture
  2. customwas evaporated
  3. extractionthe residue was extracted with dichloromethane
  4. washwashed with water
  5. dry with materialwere dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified on silica gel column

Sources & evidence

ORD record
ord-eb34614d43fa4e99a9f21f26ab822ab0
Source dataset
uspto-grants-2015_12
Patent number
US09216993B2

Reaction notes

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