Triethylamine → 3-Piperidin-1-ylpyridine-2-carbonitrile

HRID 251059ノート

反応式

HRID 251059 の反応式
[N:1]1([C:7]2[CH:8]=[N+:9]([O-])[CH:10]=[CH:11][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C[Si]([C:18]#[N:19])(C)C.C(N(CC)CC)C.C([O-])(O)=O.[Na+]>CC#N>[N:1]1([C:7]2[C:8]([C:18]#[N:19])=[N:9][CH:10]=[CH:11][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 82115Trimethylsilyl cyanideHCID 516892Sodium BicarbonateHCID 8174083-Piperidin-1-ylpyridine 1-oxide

生成物 1

HCID 230165703-Piperidin-1-ylpyridine-2-carbonitrile収率 92.2%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A mixture of 3,4,5,6-tetrahydro-2H-[1,3′]bipyridinyl 1′-oxide (1.30 g, 7.30 mmol), trimethylsilyl cyanide (1.45 g, 14.6 mmol) and triethyl amine (1.47 g, 14.6 mmol) in dry CH3CN (25 mL) was heated at reflux for 16 h, yielding a red solution. The reaction mixture was then cooled to room temperature, and saturated aqueous NaHCO3 (20 mL) was added. After concentrated under reduced pressure the mixture was extracted with CH2Cl2 (4×30 mL). The 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 (CH2Cl2) to afford 3,4,5,6-tetrahydro-2H-[1,3′]bipyridinyl-2′-carbonitrile as a pale yellow solid (1.26 g, 92%). 1H NMR (CDCl3) δ 1.58-1.66 (m, 2H), 1.75-1.83 (m, 4H), 3.21 (t, 4H, J=5.7 Hz), 7.34-7.38 (m, 2H), 8.19-8.22 (m, 1H).

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 16 h
  3. customyielding a red solution
  4. concentrationAfter concentrated under reduced pressure the mixture
  5. extractionwas extracted with CH2Cl2 (4×30 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationAfter filtration the solvent
  8. customwas removed by evaporation under vacuum
  9. customthe residue was purified by flash chromatography on a silica gel column (CH2Cl2)

出典と根拠

ORDレコード
ord-5261a34700204905bd4598be00ec2cde
出典データセット
uspto-grants-2011_01
特許番号
US07863293B2

反応ノート

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