Sodium amide → 3-(5,6,7,8-Tetrahydroquinol-8-yl)propylamine

HRID 1607038

反応式

HRID 1607038 の反応式
[N:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[NH2-].[Na+].Cl.Cl[CH2:15][CH2:16][CH2:17][NH2:18]>N>[N:1]1[C:10]2[CH:9]([CH2:15][CH2:16][CH2:17][NH2:18])[CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

参加物

5

反応物 3

HCID 24533Sodium amideHCID 663355,6,7,8-TetrahydroquinolineHCID 114690951-Propanamine, 3-chloro-, hydrochloride

生成物 1

HCID 198517793-(5,6,7,8-Tetrahydroquinol-8-yl)propylamine収率 26.5%

試薬・触媒・溶媒 1

HCID 222Ammonia溶媒

実験手順

5,6,7,8-Tetrahydroquinoline (20 g) was added quickly to sodamide (17.6 g) in liquid ammonia (250 ml) to give a dark red coloured solution. 3-Chloropropylamine hydrochloride (28.9 g) was added in portions over four hours when loss of colour was permanent after which the reaction was stirred for a further 2 hours and then quenched with ammonium chloride (20 g). The liquid ammonia was allowed to evaporate and the residues were partitioned between chloroform and water. The pH was lowered to 6 and the chloroform layer was discarded. The aqueous layer was basified (pH 12-14), and extracted with chloroform, the chloroform extracts were dried, combined, evaporated and the residue was vacuum distilled to give 3-(5,6,7,8-tetrahydroquinol-8-yl)propylamine (7.58 g), b.p. 92°-94° C. at 0.1 mm Hg.

後処理

  1. customto give a dark red coloured solution
  2. customquenched with ammonium chloride (20 g)
  3. customto evaporate
  4. customthe residues were partitioned between chloroform and water
  5. extractionextracted with chloroform
  6. dry with materialthe chloroform extracts were dried
  7. customevaporated
  8. distillationdistilled

出典と根拠

ORDレコード
ord-df8e7aeb9870434eb52d3e6a27c8d83a
出典データセット
uspto-grants-1989_09
特許番号
US04863933

関連ノート

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