1-Iodopentane → N,N-bis(pyridin-2-ylmethyl)pentan-1-amine

HRID 495261

反応式

HRID 495261 の反応式
[OH-].[K+].[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][NH:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1.I[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>CN(C)C=O>[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][N:10]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

参加物

5

反応物 3

HCID 123351-Iodopentane2 回HCID 14797Potassium HydroxideHCID 73759Bis(2-pyridylmethyl)amine

生成物 1

HCID 58794716N,N-bis(pyridin-2-ylmethyl)pentan-1-amine収率 72.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To 15 ml of N,N-dimethylformamide, 0.85 g potassium hydroxide, 1.0 g di(2-picolyl)amine, and 0.99 g 1-iodopentane were successively added. The mixture was stirred under nitrogen at 35 C for 2.5 hours before an additional 0.99 g 1-iodopentane were added. The mixture was then stirred for 16 hrs at 35 C under nitrogen. The reaction was quenched with 90 ml of water and extracted with two 50 ml portions of ethyl acetate. The combined organic layers were washed with two 25 ml portions of water, dried over anhydrous magnesium sulfate, and filtered. Following solvent removal, the orange oil obtained was purified by silica gel chromatography using a methanol/ethyl acetate mixed solvent system that was ramped from 0% to 10% methanol by volume during the course of the elution. An orange oil (0.98 g) was obtained.

後処理

  1. additionwere added
  2. customThe reaction was quenched with 90 ml of water
  3. extractionextracted with two 50 ml portions of ethyl acetate
  4. washThe combined organic layers were washed with two 25 ml portions of water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customFollowing solvent removal
  8. customthe orange oil obtained
  9. customwas purified by silica gel chromatography
  10. washwas ramped from 0% to 10% methanol by volume during the course of the elution

出典と根拠

ORDレコード
ord-d41c0e4bf5f64009af1635b1389f2716
出典データセット
uspto-grants-2009_05
特許番号
US07538931B2

関連ノート

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