Hydrochloric Acid → Piperidine-1-propylamine

HRID 1380905

反応式

HRID 1380905 の反応式
[H-].[H-].[H-].[H-].[Li+].[Al+3].[N:7]1([CH2:13][CH2:14][C:15]([NH2:17])=O)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.Cl>C1COCC1.CO>[N:7]1([CH2:13][CH2:14][CH2:15][NH2:17])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 5667843-(Piperidin-1-yl)propanamideHCID 21226445Aluminium lithium hydride

生成物 1

HCID 19049Piperidine-1-propylamine

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To an ice-cooled suspension of LiAlH4 (10.31 g, 0.27 mole) in THF (100 ml), a solution of 1-piperidine-propanamide, 4-(diphenylmethylene) 29.01 g, 0.091 mole) in THf (100 ml) was added dropwise. After stirring for 0.5 hours, the ice-bath was removed, the reaction mixture refluxed for six hours, quenched (EtOAc and 10% NaOH) and the resulting granular precipitate removed by filtration. The filtrate was concentrated to ca 20 ml, dissolved in CHCl3, washed with H2O, and the solvent removed to give a yellow-green oil. This was dissolved in MeOH, treated with HCl gas and the solvent evaporated. The residue crystallized from CH2Cl2 -Et2O to give 1-piperidinepropaneamine, 4-(diphenylmethylene)dihydrochloride hemihydrate as white solid in quantitative yield; mp 249°-252° C.

後処理

  1. customthe ice-bath was removed
  2. temperaturethe reaction mixture refluxed for six hours
  3. customquenched (EtOAc and 10% NaOH)
  4. customthe resulting granular precipitate removed by filtration
  5. concentrationThe filtrate was concentrated to ca 20 ml
  6. dissolutiondissolved in CHCl3
  7. washwashed with H2O
  8. customthe solvent removed
  9. customto give a yellow-green oil
  10. customthe solvent evaporated
  11. customThe residue crystallized from CH2Cl2 -Et2O

出典と根拠

ORDレコード
ord-f4ace30efbe543f984329973c1e60b94
出典データセット
uspto-grants-1986_04
特許番号
US04584301

関連ノート

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