Ammonium Chloride → N4-[(3R,4R)-1-benzyl-4-methyl-3-piperidinyl]-N4-methyl-2,3,4-pyridinetriamine

HRID 1696199노트

반응식

HRID 1696199 반응식
[CH2:1]([N:8]1[CH2:13][CH2:12][C@@H:11]([CH3:14])[C@@H:10]([N:15]([CH3:26])[C:16]2[CH:21]=[CH:20][N:19]=[C:18]([NH2:22])[C:17]=2[N+:23]([O-])=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[NH4+]>C(O)C.O.[Fe]>[CH2:1]([N:8]1[CH2:13][CH2:12][C@@H:11]([CH3:14])[C@@H:10]([N:15]([CH3:26])[C:16]2[CH:21]=[CH:20][N:19]=[C:18]([NH2:22])[C:17]=2[NH2:23])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 2

HCID 25517Ammonium ChlorideHCID 86635092N4-[(3R,4R)-1-benzyl-4-methyl-3-piperidinyl]-N4-methyl-3-nitro-2,4-pyridinediamine

생성물 1

HCID 68626675N4-[(3R,4R)-1-benzyl-4-methyl-3-piperidinyl]-N4-methyl-2,3,4-pyridinetriamine수율 98.3%

시약·촉매·용매 3

HCID 23925Iron촉매HCID 702Ethanol용매HCID 962Water용매

실험 절차

To a solution of N4-[(3R,4R)-1-benzyl-4-methyl-3-piperidinyl]-N4-methyl-3-nitro-2,4-pyridinediamine (230 mg) in ethanol (3.45 mL) and water (1.15 mL) were added iron powder (108 mg) and ammonium chloride (17 mg). The mixture was refluxed for 4 hours, then filtrated and extracted with 4:1 solution of chloroform and methanol. The extract was washed with saturated aqueous sodium hydrogencarbonate, dried over MgSO4 and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (chloroform:methanol=100:0:90:10) to give N4-[(3R,4R)-1-benzyl-4-methyl-3-piperidinyl]-N4-methyl-2,3,4-pyridinetriamine (207 mg) as a pale brown powder.

후처리

  1. temperatureThe mixture was refluxed for 4 hours
  2. filtrationfiltrated
  3. extractionextracted with 4:1 solution of chloroform and methanol
  4. washThe extract was washed with saturated aqueous sodium hydrogencarbonate
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (chloroform:methanol=100:0:90:10)

출처 및 근거

ORD 기록
ord-0e6dcafbad944cf7a46992cdac6d37bf
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163767B2

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