Water → benzyl N-[4-(2-azidoethyl)piperidine-1-carboximidoyl]carbamate

HRID 860

Reaction equation

HRID 860 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]([N:14]1[CH2:19][CH2:18][CH:17]([CH2:20][CH2:21]OS(C)(=O)=O)[CH2:16][CH2:15]1)=[NH:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:27]=[N+:28]=[N-:29].[Na+].O>CN(C)C=O>[N:27]([CH2:21][CH2:20][CH:17]1[CH2:18][CH2:19][N:14]([C:12](=[NH:13])[NH:11][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])[CH2:15][CH2:16]1)=[N+:28]=[N-:29]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 1403790842-[1-(N-phenylmethoxycarbonylcarbamimidoyl)piperidin-4-yl]ethyl methanesulfonate

Product 1

HCID 140379074benzyl N-[4-(2-azidoethyl)piperidine-1-carboximidoyl]carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

In 100 ml of dimethylformamide was dissolve (0.0115 mol) of crude 1-benzyloxycarbonylamidino-4-mesyloxyethyl piperidine and 4.5 g (0.069 mol) of sodium azide was added. The mixture was heated at 100° C. for 2.5 h. It was then poured into water and extracted with ethyl acetate three times. The combined organic phase was washed with water, dried (Na2SO4) and evaporated. The residue was flash chromatographed on silica gel using ethyl acetate/heptane 1/1 as eluent. Yield: 3.0 g (79%).

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate three times
  3. washThe combined organic phase was washed with water
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customchromatographed on silica gel

Sources & evidence

ORD record
ord-d3631dc5ac684ec9b01dd5b9b7ce5987
Source dataset
uspto-grants-1998_03
Patent number
US05723444

Linked notes

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