Thionyl Chloride → 2-(chloromethyl)-3-hydroxy-6-methyl-1-(2,2,2-trifluoroethyl)pyridin-4(1H)-one hydrochloride

HRID 1519037ノート

反応式

HRID 1519037 の反応式
[OH:1][C:2]1[C:7](=[O:8])[CH:6]=[C:5]([CH3:9])[N:4]([CH2:10][C:11]([F:14])([F:13])[F:12])[C:3]=1[CH2:15]O.S(Cl)([Cl:19])=O>C(#N)C>[ClH:19].[Cl:19][CH2:15][C:3]1[N:4]([CH2:10][C:11]([F:14])([F:13])[F:12])[C:5]([CH3:9])=[CH:6][C:7](=[O:8])[C:2]=1[OH:1]

参加物

4

反応物 2

HCID 24386Thionyl ChlorideHCID 668692313-hydroxy-2-(hydroxymethyl)-6-methyl-1-(2,2,2-trifluoroethyl)pyridin-4(1H)-one

生成物 1

HCID 866728102-(chloromethyl)-3-hydroxy-6-methyl-1-(2,2,2-trifluoroethyl)pyridin-4(1H)-one hydrochloride

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

3-Hydroxy-2-(hydroxymethyl)-6-methyl-1-(2,2,2-trifluoroethyl)pyridin-4(1H)-one (375 mg, 1.6 mmol) was mixed with acetonitrile at 80° C. and the thionyl chloride (753 mg, 6.3 mmol) was added. The reaction mixture was stirred for 5 minutes and then concentrated by rotary evaporator to give 2-(chloromethyl)-3-hydroxy-6-methyl-1-(2,2,2-trifluoroethyl)pyridin-4(1H)-one hydrochloride. The chloride compound was added to a solution of piperidine (672 mg, 7.9 mmol) in isopropanol (5 mL) at room temperature. Five minutes later, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water twice and brine, dried and concentrated. The residue was triturated with ether/hexanes to give 3-hydroxy-6-methyl-2-(piperidin-1-ylmethyl)-1-(2,2,2-trifluoroethyl)pyridin-4(1H)-one (165 mg) as pale orange solid. Yield=34%; 1H NMR (MeOD-D4, 90 MHz) δ (ppm): 6.37 (s, 1H), 3.72 (br. s, 2H), 2.45 (br. m, 7H) and 1.51 (br. m, 6H); MS m/z 305 [M+1]+.

後処理

  1. concentrationconcentrated by rotary evaporator

出典と根拠

ORDレコード
ord-03b4240580b041d4a20f89fe66e446c8
出典データセット
uspto-grants-2015_07
特許番号
US09073865B2

反応ノート

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