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

HRID 1589539ノート

反応式

HRID 1589539 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a9f06906c74d4cd39179bef628917988
出典データセット
uspto-grants-1986_02
特許番号
US04571394

反応ノート

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