Potassium Iodide → 5-(Piperidin-1-yl)pentan-1-amine

HRID 604392

反応式

HRID 604392 の反応式
Cl[CH2:2][CH2:3][CH2:4][CH2:5][C:6]#[N:7].[NH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[H-].[Al+3].[Li+].[H-].[H-].[H-].[Na].C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[K+]>C(O)C.O1CCCC1.O>[N:7]1([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][NH2:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

10

反応物 6

HCID 4875Potassium IodideHCID 8082PiperidineHCID 11430Potassium CarbonateHCID 804745-ChlorovaleronitrileHCID 21226445Aluminium lithium hydrideHCID 86594854HCID 86594854、化合物

生成物 1

HCID 71384475-(Piperidin-1-yl)pentan-1-amine収率 59%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

5-Chlorovaleronitrile (10 mmol), 20 mmol of piperidine, 20 mmol of potassium carbonate and a catalytic amount of potassium iodide in 50 ml of ethanol were refluxed for 6 hours. The solvent was removed under reduced pressure, the residue suspended in water and extracted with methylene chloride. The organic layer was purified by column chromatography on silica gel using methylene chloride/methanol/aqueous ammonia (90/10/1) as eluent (Yield: 59%). The product was added dropwise to a suspension of 25 mmol of lithium aluminium hydride in 25 ml of dry tetrahydrofurane at 0° C. After refluxing for 1 hour 10 ml of a saturated solution of sodium/potassium tartrate in water was added dropwise. The residue was filtered off and the filtrate purified by column chromatography on silica gel using methylene chloride/methanol/aqueous ammonia (90/10/1) as eluent. The residue was crystallized with hydrochloric acid from diethyl ether/2-propanol.

後処理

  1. customThe solvent was removed under reduced pressure
  2. extractionextracted with methylene chloride
  3. customThe organic layer was purified by column chromatography on silica gel
  4. additionwas added dropwise
  5. filtrationThe residue was filtered off
  6. customthe filtrate purified by column chromatography on silica gel
  7. customThe residue was crystallized with hydrochloric acid from diethyl ether/2-propanol

出典と根拠

ORDレコード
ord-a848a1a768d44709b5ed7825f960b825
出典データセット
uspto-grants-2011_03
特許番号
US07910605B2

関連ノート

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