Sodium Azide → HCID 10381414, compound

HRID 854319Notes

Reaction equation

HRID 854319 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][CH:9]1[CH2:21]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:23]=[N+:24]=[N-:25].[Na+]>CN(C)C=O.C(=O)(O)[O-].[Na+].O>[N:23]([CH2:21][CH:9]1[CH2:10][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:12][CH2:13][N:8]1[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[N+:24]=[N-:25]

Participants

6

Reactant 2

HCID 33557Sodium AzideHCID 106631191,4-Dibenzyl-2-(chloromethyl)piperazine

Product 1

HCID 10381414HCID 10381414, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 1,4-dibenzyl-2-chloromethyl-piperazine (8.8 g, 0.028 mol) in dimethylformamide (90 mL) under nitrogen was added sodium azide (5.5 g) and the reaction stirred at 50° C. for 18 h. The reaction was cooled and diluted with 10% aqueous sodium bicarbonate (100 mL) and water (250 mL) and the mixture extracted with ethyl acetate (2×200 mL). The organic extracts were washed with 10% sodium bicarbonate, brine, dried over sodium sulfate and concentrated to an oil.

Workup

  1. temperatureThe reaction was cooled
  2. extractionthe mixture extracted with ethyl acetate (2×200 mL)
  3. washThe organic extracts were washed with 10% sodium bicarbonate, brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to an oil

Sources & evidence

ORD record
ord-d9f69f11173b41aabce8747d6ef38b76
Source dataset
uspto-grants-2007_08
Patent number
US07259157B2

Reaction notes

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