Sodium Azide → HCID 15480811, compound

HRID 1058609Notes

Reaction equation

HRID 1058609 reaction equation
CS(O[CH2:6][CH:7]1[CH2:12][CH2:11][N:10]([C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][CH2:8]1)(=O)=O.[N-:32]=[N+:33]=[N-:34].[Na+]>CN(C)C=O>[N:32]([CH2:6][CH:7]1[CH2:12][CH2:11][N:10]([C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][CH2:8]1)=[N+:33]=[N-:34]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 15480809HCID 15480809, compound

Product 1

HCID 15480811HCID 15480811, compoundYield 80.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A suspension of 60.0 g of (N-triphenylmethyl-4-piperidyl)methyl methanesulfonate and 17.9 g of sodium azide in 300 ml of dried N,N-dimethyl-formamide was stirred at 70° C. for 17 hours. After the reaction, an insoluble matter was filtered off and the filtrate was concentrated. The resulting residue was added with water and extracted with ethyl acetate. The extract was washed successively with water and saturated brine, and dried, and then the solvent was evaporated. The resulting solid was washed successively with ethanol and n-hexane to give 42.6 g of colorless crystals. Recrystallization from a mixture of methanol and diethyl ether gave colorless crystals having the melting point of from 103.5 to 105.5° C.

Workup

  1. customAfter the reaction
  2. filtrationan insoluble matter was filtered off
  3. concentrationthe filtrate was concentrated
  4. additionThe resulting residue was added with water
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed successively with water and saturated brine
  7. customdried
  8. customthe solvent was evaporated
  9. washThe resulting solid was washed successively with ethanol and n-hexane

Sources & evidence

ORD record
ord-4bb9a37c741a47869427ae9baaf8ecc5
Source dataset
uspto-grants-2003_02
Patent number
US06518265B1

Reaction notes

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