Hydrochloric Acid → N-(phenylcarbamoylamino)-1,2,3,6-tetrahydropyridine

HRID 4364ノート

反応式

HRID 4364 の反応式
[C:1]1([NH:7][C:8]([N:10]=[N+:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH2:12]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+].Cl>C(O)C.O>[C:1]1([NH:7][C:8]([NH:10][N:11]2[CH2:12][CH:13]=[CH:14][CH2:15][CH2:16]2)=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 20152386N-(phenylcarbamoylimino)pyridinium

生成物 1

HCID 13534718N-(phenylcarbamoylamino)-1,2,3,6-tetrahydropyridine

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

To a solution of N-(phenylcarbamoylimino)pyridinium ylide (0.64 g) in a mixture of ethanol (30 ml) and water (10 ml) was added sodium borohydride (0.20 g) at ambient temperature. After being stirred for 4 hours, the reaction mixture was acidified with 1N hydrochloric acid, concentrated to a volume of ca. 15 ml. The crystalline precipitate was collected, washed with water and dried in vacuo. The crude product was dissolved in ethyl acetate and extracted with 10% hydrochloric acid (20 ml). The extract was adjusted to pH 3 with aqueous sodium bicarbonate and extracted with ethyl acetate (30 ml). The organic layer was washed with aqueous sodium bicarbonate (10 ml), dried over magnesium sulfate and evaporated to give N-(phenylcarbamoylamino)-1,2,3,6-tetrahydropyridine (0.28 g), which was recrystallized from ethyl acetate to afford colorless needles (0.15 g). mp: 157°-159° C.

後処理

  1. concentrationconcentrated to a volume of ca. 15 ml
  2. customThe crystalline precipitate was collected
  3. washwashed with water
  4. customdried in vacuo
  5. dissolutionThe crude product was dissolved in ethyl acetate
  6. extractionextracted with 10% hydrochloric acid (20 ml)
  7. extractionextracted with ethyl acetate (30 ml)
  8. washThe organic layer was washed with aqueous sodium bicarbonate (10 ml)
  9. dry with materialdried over magnesium sulfate
  10. customevaporated

出典と根拠

ORDレコード
ord-4dac31e8682a4872921ace479cd32233
出典データセット
uspto-grants-1988_02
特許番号
US04725608

反応ノート

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