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

HRID 1696199ノート

反応式

HRID 1696199 の反応式
[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

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-0e6dcafbad944cf7a46992cdac6d37bf
出典データセット
uspto-grants-2012_04
特許番号
US08163767B2

反応ノート

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