Thionyl Chloride → Benzylmethyl-(2-pyridin-3-ylcyclohex-1-enylmethyl)amine

HRID 131533ノート

反応式

HRID 131533 の反応式
Cl.[CH2:2]([CH2:9][NH:10][CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][C:13]1([C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1)O)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.S(Cl)(Cl)=O>>[CH2:2]([CH2:9][NH:10][CH2:11][C:12]1[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=1[C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

参加物

3

反応物 2

HCID 24386Thionyl ChlorideHCID 692216432-[(Benzylmethylamino)methyl]-1-pyridin-3-ylcyclohexanol hydrochloride

生成物 1

HCID 69220350Benzylmethyl-(2-pyridin-3-ylcyclohex-1-enylmethyl)amine収率 26.5%

実験手順

5.5 g 2-[(benzylmethylamino)methyl]-1-pyridin-3-ylcyclohexanol hydrochloride and 27.5 ml thionyl chloride were heated at a bath temperature of 75° C. for one hour. After the mixture had been concentrated in vacuo, the residue was taken up in ethyl acetate and sodium hydroxide solution (32 percent strength by weight) and the organic phase was separated off, dried and concentrated. The crude product obtained (3.7 g) was chromatographed on silica gel with diisopropyl ether/ethyl acetate (V/V=2:1). 1.23 g benzylmethyl-(2-pyridin-3-ylcyclohex-1-enylmethyl)amine were obtained, and were dissolved in approx. 25 ml acetone and converted into the corresponding hydrochloride with 1.66 μl water and 1.18 ml chlorotrimethylsilane.

後処理

  1. concentrationAfter the mixture had been concentrated in vacuo
  2. customsodium hydroxide solution (32 percent strength by weight) and the organic phase was separated off
  3. customdried
  4. concentrationconcentrated
  5. customThe crude product obtained (3.7 g)
  6. customwas chromatographed on silica gel with diisopropyl ether/ethyl acetate (V/V=2:1)

出典と根拠

ORDレコード
ord-20e1fc51fa9244bca99efad335635a73
出典データセット
uspto-grants-2008_06
特許番号
US07384961B2

反応ノート

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