Hydrochloric Acid → HCID 69221757, compound

HRID 131536Notes

Reaction equation

HRID 131536 reaction equation
Cl.[CH3:2][N:3]([CH3:17])[CH2:4][C:5]1[CH2:6][O:7][CH2:8][CH2:9][C:10]=1[C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1.O.[Cl:19][Si](C)(C)C>C(O)C>[ClH:19].[CH3:2][N:3]([CH3:17])[CH2:4][C:5]1[CH2:6][O:7][CH2:8][CH2:9][C:10]=1[C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6397ChlorotrimethylsilaneHCID 69221758HCID 69221758, compound

Product 1

HCID 69221757HCID 69221757, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4.95 g of a mixture of cis- and trans-3-dimethylaminomethyl-4-pyridin-3-yl-tetrahydropyran-4-ol hydrochloride and 6.6 ml thionyl chloride were stirred at a bath temperature of 65° C. for two hours and then overnight at room temperature. 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 (2.2 g) was chromatographed on silica gel with a mixture of equal volumes of methanol and methylene chloride. In addition to 0.82 g of the target product, a mixed fraction of 1.26 g was obtained, which was chromatographed again under analogous conditions. A total of 0.96 g of the target product was obtained in this way, and was dissolved in approx. 10 ml ethanol and converted into the corresponding hydrochloride of dimethyl-(4-pyridin-3-yl-5,6-dihydro-2H-pyran-3-yl-methyl)amine with a melting point of 244-248° C. with 0.18 ml water and 1.23 ml chlorotrimethylsilane.

Sources & evidence

ORD record
ord-542acd70108c4349b3c1eb964f7fa20f
Source dataset
uspto-grants-2008_06
Patent number
US07384961B2

Reaction notes

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