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

HRID 131533노트

반응식

HRID 131533 반응식
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

참가 물질

3

반응물 2

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

생성물 1

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

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-20e1fc51fa9244bca99efad335635a73
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384961B2

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