Water → 4-(3'-Azidopropyl)-piperidine

HRID 903863

Reaction equation

HRID 903863 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].Br.Br[CH2:7][CH2:8][CH2:9][CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.O>CO>[N:1]([CH2:7][CH2:8][CH2:9][CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 135032154-(3-Bromopropyl)piperidine hydrobromide

Product 1

HCID 135032204-(3'-Azidopropyl)-piperidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium azide (1 g) was added to a mixture of 4-(3'-bromopropyl)-piperidine hydrobromide (2 g), water (7 ml) and methanol (7 ml). The pH of the mixture was adjusted to 6.3, and the resulting solution was refluxed for 2 hours. After cooling, methanol was evaporated, 30 percent aqueous sodium hydroxide was added and the mixture was extracted several times with ether. The ether extracts were dried and evaporated to leave the desired compound as an oil. The IR-spectrum (CHCl3) showed strong bands at 2925, 2100 and 1450 cm-1.

Workup

  1. temperaturethe resulting solution was refluxed for 2 hours
  2. temperatureAfter cooling
  3. custommethanol was evaporated
  4. addition30 percent aqueous sodium hydroxide was added
  5. extractionthe mixture was extracted several times with ether
  6. dry with materialThe ether extracts were dried
  7. customevaporated

Sources & evidence

ORD record
ord-806b04d0240c4ed3bee89453fef8cddb
Source dataset
uspto-grants-1980_10
Patent number
US04229443

Linked notes

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