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

HRID 2164741Notes

Reaction equation

HRID 2164741 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 101%

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 give 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

Sources & evidence

ORD record
ord-185f89f8ed3742c7b1b78411627379bf
Source dataset
uspto-grants-1985_03
Patent number
US04507296

Reaction notes

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