Hydrochloric Acid → benzyl N-[4-(2-aminoethyl)piperidine-1-carboximidoyl]carbamate

HRID 861

반응식

HRID 861 반응식
[BH4-].[Na+].[N:3]([CH2:6][CH2:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14](=[NH:26])[NH:15][C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH2:10][CH2:9]1)=[N+]=[N-].Cl>O.O1CCCC1.[Pd]>[NH2:3][CH2:6][CH2:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14](=[NH:26])[NH:15][C:16]([O:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[O:17])[CH2:10][CH2:9]1

참가 물질

7

반응물 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 140379074benzyl N-[4-(2-azidoethyl)piperidine-1-carboximidoyl]carbamate

생성물 1

HCID 140379088benzyl N-[4-(2-aminoethyl)piperidine-1-carboximidoyl]carbamate

시약·촉매·용매 3

HCID 23938Palladium촉매2회HCID 962Water용매3회HCID 8028Tetrahydrofuran용매

실험 절차

To 30 ml of water was added 0.40 g of 10% Pd/C. Sodium borohydride, 1.0 g (0.031 mol), was dissolved in 30 ml of water and was added carefully to the stirred and ice-cooled slurry of Pd/C and water. 4-Azidoethyl-1-benzyloxycarbonylamidino piperidine, 2.9 g (8.8 mmol), was dissolved in 80 ml of tetrahydrofurane and this solution was added dropwise to the ice-cooled aqueous slurry above. After 4 h of stirring at room temperature the mixture was ice-cooled again and 30 ml of 2M HCl was added. The mixture was filtered through celite and the celite was rinsed with additional water. The tetrahydrofuran was evaporated and the aqueous phase was washed with ethyl acetate. The aqueous phase was made alkaline with 2M NaOH and extracted with methylene chloride three times. The combined organic phase was washed with water, dried (Na2SO4) and evaporated. The product was used in the following step without further purification.

후처리

  1. additionwas added carefully to the
  2. temperaturecooled aqueous slurry above
  3. stirringAfter 4 h of stirring at room temperature the mixture
  4. temperaturecooled again
  5. filtrationThe mixture was filtered through celite
  6. washthe celite was rinsed with additional water
  7. customThe tetrahydrofuran was evaporated
  8. washthe aqueous phase was washed with ethyl acetate
  9. extractionextracted with methylene chloride three times
  10. washThe combined organic phase was washed with water
  11. dry with materialdried (Na2SO4)
  12. customevaporated
  13. customThe product was used in the following step without further purification

출처 및 근거

ORD 기록
ord-2080a877db5f4bf4b20e375ca34bad46
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05723444

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