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

HRID 131533Notes

Reaction equation

HRID 131533 reaction equation
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

Participants

3

Reactant 2

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

Product 1

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

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-20e1fc51fa9244bca99efad335635a73
Source dataset
uspto-grants-2008_06
Patent number
US07384961B2

Reaction notes

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