Sodium Azide → HCID 59657561, compound

HRID 1866036Notes

Reaction equation

HRID 1866036 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Br:23])([C:14](O)=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC(N(C)C)=C(C)C.[N-:32]=[N+:33]=[N-:34].[Na+]>ClCCl.COC(C)(C)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:14]([N:32]=[N+:33]=[N-:34])=[O:15])([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Br:23])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 33557Sodium AzideHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 497602304-(2-Bromophenyl)-1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid

Product 1

HCID 59657561HCID 59657561, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

To a solution of 2.00 g (5.20 mmol) 4-(2-bromo-phenyl)-piperidine-1,4-dicarboxylic acid mono-tert-butyl ester in 26 ml dichloromethane were added 0.76 ml (5.73 mmol) 1-chloro-N,N,2-trimethylpropenylamine at room temperature. After stirring for 45 min the reaction mixture was concentrated in vacuo. The residual oil was redissolved in 26 ml dry N,N-dimethylformamide and treated with 0.51 g (7.8 mmol) sodium azide. After stirring for 1 h the reaction mixture was diluted with 200 ml tert-butyl methyl ether and washed with 0.5 M aqueous sodium carbonate solution (2×50 ml). The combined aqueous layers were extracted with tert-butyl methyl ether (2×100 ml). The combined organic layers were washed with water (1×50 ml) and brine (1×50 ml), dried over sodium sulfate and concentrated in vacuo to give the crude title compound (1.76 g, 83%) as a light yellow solid.

Workup

  1. concentrationwas concentrated in vacuo
  2. dissolutionThe residual oil was redissolved in 26 ml dry N,N-dimethylformamide
  3. stirringAfter stirring for 1 h the reaction mixture
  4. washwashed with 0.5 M aqueous sodium carbonate solution (2×50 ml)
  5. extractionThe combined aqueous layers were extracted with tert-butyl methyl ether (2×100 ml)
  6. washThe combined organic layers were washed with water (1×50 ml) and brine (1×50 ml)
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-16188268f3e44d54a6e3adc02af2e236
Source dataset
uspto-grants-2009_12
Patent number
US07629353B2

Reaction notes

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