Ammonium Chloride → HCID 68814041, compound

HRID 2105234Notes

Reaction equation

HRID 2105234 reaction equation
[C:1]([O:5][N:6]1[CH2:10][CH2:9][CH2:8][CH:7]1[C:11]#[N:12])([CH3:4])([CH3:3])[CH3:2].[N-:13]=[N+:14]=[N-:15].[Na+].[Cl-].[NH4+]>CN(C=O)C>[C:1]([O:5][N:6]1[CH2:10][CH2:9][CH2:8][CH:7]1[C:11]1[N:13]=[N:14][NH:15][N:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 68813487HCID 68813487, compound

Product 1

HCID 68814041HCID 68814041, compoundYield 24.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of tert-butyloxy-2-cyanopyrrolidine (3 g, 15.3 mmol), sodium azide (1.49 g, 23.0 mmol) and ammonium chloride (1.22 g, 23 mmol) in DMF (15 ml) were heated at 95° C. for 48 hours. The reaction was then partitioned between ethyl acetate and water. The organics were separated, dried (MgSO4) and the volatiles removed by evaporation. The residue was triturated with diethyl ether and collected by filtration to give the title compound (0.79 g, 22%) as a white solid.

Workup

  1. customThe reaction was then partitioned between ethyl acetate and water
  2. customThe organics were separated
  3. dry with materialdried (MgSO4)
  4. customthe volatiles removed by evaporation
  5. customThe residue was triturated with diethyl ether
  6. filtrationcollected by filtration

Sources & evidence

ORD record
ord-6a3153792772473397fd013504311dbc
Source dataset
uspto-grants-2009_08
Patent number
US07579349B2

Reaction notes

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