Chlorotrimethylsilane → Dimethylaminomethyl-1-pyridin-3-yl-cyclohexanol hydrochloride

HRID 131522

반응식

HRID 131522 반응식
C([Li])CCC.Br[C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1.[CH3:13][N:14]([CH2:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][C:18]1=[O:23])[CH3:15].[Cl:24][Si](C)(C)C>C(OCC)C.C(O)C.O>[ClH:24].[CH3:15][N:14]([CH2:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][C:18]1([C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)[OH:23])[CH3:13]

참가 물질

8

반응물 4

HCID 6397ChlorotrimethylsilaneHCID 122863-BromopyridineHCID 858382-((Dimethylamino)methyl)cyclohexanoneHCID 178418339Butyllithium

생성물 1

HCID 69220231Dimethylaminomethyl-1-pyridin-3-yl-cyclohexanol hydrochloride

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매2회HCID 3283Diethyl Ether용매2회

반응 조건

온도
-30 °C

실험 절차

224 ml n-butyllithium solution (2.5 mol/l in hexane) were added dropwise to a solution of 54 ml 3-bromopyridine in 750 ml analytical grade diethyl ether in the course of 30 minutes at a temperature of −35 to −40° C. After a further 20 minutes at this temperature, 86.9 g 2-dimethylaminomethylcyclohexanone, dissolved in 90 ml analytical grade diethyl ether, were added dropwise in the course of 30 minutes, with continued cooling, and the mixture was stirred again for 60 minutes with gentle warming to −30° C. 150 ml water were then added with warming of the reaction mixture to 0° C., the phases were separated, the aqueous phase was extracted twice with ethyl acetate, the combined organic phases were dried over magnesium sulfate and filtered and the filtrate was concentrated. The crude product obtained (139 g) was dissolved in 700 ml absolute ethanol, and 142 ml chlorotrimethylsilane and 20.2 ml water were added in succession and the mixture was stirred in an ice-bath for 12 hours. The solid which had precipitated out was filtered off with suction, washed with a little absolute ethanol and dried at 90° C. in vacuo (approx. 50 mbar) for two hours. 63.9 g 2-dimethylaminomethyl-1-pyridin-3-yl-cyclohexanol hydrochloride were obtained.

후처리

  1. additionwere added dropwise in the course of 30 minutes, with continued cooling
  2. temperaturewith warming of the reaction mixture to 0° C.
  3. customthe phases were separated
  4. extractionthe aqueous phase was extracted twice with ethyl acetate
  5. dry with materialthe combined organic phases were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated
  8. customThe crude product obtained (139 g)
  9. stirringthe mixture was stirred in an ice-bath for 12 hours
  10. customThe solid which had precipitated out
  11. filtrationwas filtered off with suction
  12. washwashed with a little absolute ethanol
  13. customdried at 90° C. in vacuo (approx. 50 mbar) for two hours

출처 및 근거

ORD 기록
ord-46191ac03dfe479bb1d555ed69624bf6
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384961B2

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