Triethylamine → N-[1-(3,4-Difluorobenzyl)-piperidinyl]-3-hydrazinocarbonyl-propionamide

HRID 968270노트

반응식

HRID 968270 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[F:16])[CH2:5][N:6]1[CH2:11][CH2:10][CH:9](N)[CH2:8][CH2:7]1.C([N:19](CC)CC)C.C[O:25][C:26](=O)[CH2:27][CH2:28][C:29](Cl)=O.[OH2:33].[NH2:34][NH2:35]>ClCCl.C(O)C.O>[F:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[F:16])[CH2:5][N:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]1[NH:19][C:26](=[O:25])[CH2:27][CH2:28][C:29]([NH:34][NH2:35])=[O:33]

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 73888Butanoic acid, 4-chloro-4-oxo-, methyl esterHCID 180021391-[(3,4-Difluorophenyl)methyl]piperidin-4-amine

생성물 1

HCID 69744306N-[1-(3,4-Difluorobenzyl)-piperidinyl]-3-hydrazinocarbonyl-propionamide

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

A solution of 1-(3,4-difluorobenzyl)-piperidin-4-ylamine (8.7 g; EP-A2-0625507) and triethylamine (7.0 ml) in dichloromethane (200 ml) stirring at ambient temperature was treated with 3-chlorocarbonyl-propionic acid methyl ester (5.2 ml). After stirring for 16 hours, the reaction mixture was washed with brine, the organic layer was dried (MgSO4), and evaporated to leave a white solid. This solid was suspended in ethanol (200 ml), treated with hydrazine hydrate (5 ml) and the resulting mixture was stirred at reflux for 16 hours and then allowed to cool. Water (30 ml) was added to the reaction mixture and the ethanol was evaporated. The aqueous residue was then extracted into dichloromethane (6×50 ml), the combined organics were dried (MgSO4) and evaporated to give the subtitle compound as a white solid. (4.8 g)

후처리

  1. washthe reaction mixture was washed with brine
  2. dry with materialthe organic layer was dried (MgSO4)
  3. customevaporated
  4. customto leave a white solid
  5. stirringthe resulting mixture was stirred
  6. temperatureat reflux for 16 hours
  7. temperatureto cool
  8. customthe ethanol was evaporated
  9. extractionThe aqueous residue was then extracted into dichloromethane (6×50 ml)
  10. dry with materialthe combined organics were dried (MgSO4)
  11. customevaporated

출처 및 근거

ORD 기록
ord-6a35c06c54a64f2b9cca82b12d5cf558
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06958350B2

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