Sodium Azide → HCID 86693822, compound

HRID 538006Notes

Reaction equation

HRID 538006 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].CS(O[CH:10]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:11][CH2:12][N:13]1[CH2:16][CH2:15][CH2:14]1)(=O)=O>CN(C=O)C>[N:1]([CH:10]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:11][CH2:12][N:13]1[CH2:14][CH2:15][CH2:16]1)=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 77230729HCID 77230729, compound

Product 1

HCID 86693822HCID 86693822, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.4 1.50 g (23.1 mmol) of sodium azide are added to a solution of 2.00 g (7.43 mmol) of 3-azetidin-1-yl-1-phenylpropyl methanesulfonate in 50 ml of DMF, and the mixture is stirred at room temperature for 48 hours. The reaction mixture is partitioned between water and ethyl acetate. The organic phase is dried over sodium sulfate, evaporated, and the residue is chromatographed on a silica-gel column with ethyl acetate/methanol as eluent: 1-(3-azido-3-phenylpropyl)azetidine as colourless viscous oil; HPLC/MS 0.9 min; [M+H] 217.

Workup

  1. customThe reaction mixture is partitioned between water and ethyl acetate
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. customevaporated
  4. customthe residue is chromatographed on a silica-gel column with ethyl acetate/methanol as eluent
  5. customHPLC/MS 0.9 min

Sources & evidence

ORD record
ord-461561c861cb4c48a3cf1b8d6ccdbbf9
Source dataset
uspto-grants-2014_10
Patent number
US08865715B2

Reaction notes

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