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

HRID 604392

반응식

HRID 604392 반응식
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

참가 물질

10

반응물 6

HCID 4875Potassium IodideHCID 8082PiperidineHCID 11430Potassium CarbonateHCID 804745-ChlorovaleronitrileHCID 21226445Aluminium lithium hydrideHCID 86594854HCID 86594854, 화합물

생성물 1

HCID 71384475-(Piperidin-1-yl)pentan-1-amine수율 59%

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a848a1a768d44709b5ed7825f960b825
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07910605B2

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