Ammonium Chloride → 1-Azido-4-[3-(1-piperidinylmethyl)phenoxy]-2-butanol

HRID 1589539Notes

Reaction equation

HRID 1589539 reaction equation
[O:1]1[CH2:3][CH:2]1[CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]([CH2:13][N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:10]=[CH:11][CH:12]=1.[N-:20]=[N+:21]=[N-:22].[Na+].[Cl-].[NH4+]>C(O)C>[N:20]([CH2:3][CH:2]([OH:1])[CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:8]=1)=[N+:21]=[N-:22]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 544347281-[[3-(2-Oxiranylethoxy]phenyl]methyl]piperidine

Product 1

HCID 202460071-Azido-4-[3-(1-piperidinylmethyl)phenoxy]-2-butanolYield 53%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-[[3-[2-oxiranylethoxy]phenyl]methyl]piperidine (17 g), sodium azide (5.1 g) and ammonium chloride (2.73 g) in 25% aqueous ethanol (200 ml) was refluxed for 6 h and concentrated to ca. 130 ml. The concentrate was diluted with water (50 ml), saturated with potassium carbonate and extracted with isopropanol. The extract was dried and evaporated to given an oil (20 g) which was chromatographed on silica using dichloromethane:ethanol:ammonia (200:8:1) to give the title compound (10.5 g) as a colourless oil.

Workup

  1. concentrationconcentrated to ca. 130 ml
  2. additionThe concentrate was diluted with water (50 ml), saturated with potassium carbonate
  3. extractionextracted with isopropanol
  4. customThe extract was dried
  5. customevaporated
  6. customwas chromatographed on silica

Sources & evidence

ORD record
ord-a9f06906c74d4cd39179bef628917988
Source dataset
uspto-grants-1986_02
Patent number
US04571394

Reaction notes

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