Potassium Carbonate → (3,5-Dimethyl-pyridin-2-ylmethyl)-(4-pyrrolidin-1-yl-butyl)-amine

HRID 251072

反応式

HRID 251072 の反応式
[N:1]1([CH2:6][CH2:7][CH2:8][CH2:9][NH2:10])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:11][C:12]1[C:13]([CH:19]=O)=[N:14][CH:15]=[C:16]([CH3:18])[CH:17]=1.C([O-])([O-])=O.[K+].[K+].[BH4-].[Na+]>CO.O>[CH3:11][C:12]1[C:13]([CH2:19][NH:10][CH2:9][CH2:8][CH2:7][CH2:6][N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[N:14][CH:15]=[C:16]([CH3:18])[CH:17]=1

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 27627624-(Pyrrolidin-1-yl)butan-1-amineHCID 4311764Sodium borohydrideHCID 187316833,5-Dimethylpyridine-2-carbaldehyde

生成物 1

HCID 67271736(3,5-Dimethyl-pyridin-2-ylmethyl)-(4-pyrrolidin-1-yl-butyl)-amine収率 33.1%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

A mixture of 4-pyrrolidin-1-yl-butylamine (0.180 g, 1.27 mmol) (Seguin, H. et al. Synth. Commun. 1998, 28, 4257-4272), 3,5-dimethyl-pyridine-2-carbaldehyde (0.171 g, 1.27 mmol) and K2CO3 (0.175 g, 1.27) in MeOH (5 mL) was stirred for 20 h. The mixture was filtered through a celite cake and the filtrate was cooled at 0° C. NaBH4 (0.048 g, 1.3 mmol) was added to the filtrate, and the mixture was stirred at for 1 h. Water (20 mL) was added and MeOH was removed. The aqueous residue was extracted with CH2Cl2 (3×20 mL). The organic extracts were combined and dried over anhydrous Na2SO4. After filtration the solvent was removed by evaporation under vacuum, and the residue was purified by flash chromatography on a silica gel column (100:5:3 CH2Cl2/MeOH/NH4OH), affording (3,5-dimethyl-pyridin-2-ylmethyl)-(4-pyrrolidin-1-yl-butyl)-amine as a colorless oil (0.110 g, 33%). 1H NMR (CDCl3) δ 1.54-1.58 (m, 4H), 1.72-1.76 (m, 4H), 2.24 (s, 3H), 2.25 (s, 3H), 2.39-2.46 (m, 6H), 2.66-2.71 (m, 2H), 3.81 (s, 2H), 7.21 (s, 1H), 8.18 (s, 1H).

後処理

  1. filtrationThe mixture was filtered through a celite cake
  2. stirringthe mixture was stirred at for 1 h
  3. customMeOH was removed
  4. extractionThe aqueous residue was extracted with CH2Cl2 (3×20 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationAfter filtration the solvent
  7. customwas removed by evaporation under vacuum
  8. customthe residue was purified by flash chromatography on a silica gel column (100:5:3 CH2Cl2/MeOH/NH4OH)

出典と根拠

ORDレコード
ord-1b4077db23e34f339936f9716915d655
出典データセット
uspto-grants-2011_01
特許番号
US07863293B2

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