Water → HCID 69222226, 화합물

HRID 131523

반응식

HRID 131523 반응식
S(Cl)([Cl:3])=O.Cl.[CH3:6][N:7]([CH2:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C:11]1([C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)O)[CH3:8].[Cl:23][Si](C)(C)C.O>C(O)C>[ClH:3].[ClH:23].[CH3:6][N:7]([CH3:8])[CH2:9][C:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=1[C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 6397ChlorotrimethylsilaneHCID 24386Thionyl ChlorideHCID 69220231Dimethylaminomethyl-1-pyridin-3-yl-cyclohexanol hydrochloride

생성물 1

HCID 69222226HCID 69222226, 화합물

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
62.5 °C

실험 절차

129 ml thionyl chloride were added dropwise to 74.9 g 2-dimethylaminomethyl-1-pyridin-3-yl-cyclohexanol hydrochloride with vigorous evolution of gas, and the mixture was heated at 60 to 65° C. for 2.5 hours, while stirring, and was then concentrated under a water pump. After cooling, first 200 ml water and then 100 ml sodium hydroxide solution (32 per cent strength by weight) were added, the mixture was then extracted twice with 250 ml of a mixture of equal volumes of tetrahydrofuran and ethyl acetate each time, the combined extracts were dried over magnesium sulfate and filtered and the filtrate was concentrated. The crude product obtained (48.9 g) was dissolved in 350 ml absolute ethanol, and 57.4 ml chlorotrimethylsilane and 8.1 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. 34.7 g of crude dimethyl-(2-pyridin-3-yl-cyclohex-1-enylmethyl)amine dihydrochloride were obtained. For final purification, 168 g of crude dimethyl-(2-pyridin-3-yl-cyclohex- 1-enylmethyl)amine dihydrochloride prepared according to the above instructions were dissolved in 650 ml of boiling absolute ethanol and crystallized again by cooling in an ice-bath, while stirring. After the crystals had been stirred overnight at room temperature, they were filtered off with suction, washed with a little absolute ethanol and dried at 120° C. in vacuo (approx. 50 mbar) for 4.5 hours. 121 g dimethyl-(2-pyridin-3-yl-cyclohex- 1-enylmethyl)amine dihydrochloride with a melting point of 215 to 218° C. were obtained.

후처리

  1. concentrationwas then concentrated under a water pump
  2. temperatureAfter cooling
  3. additionfirst 200 ml water and then 100 ml sodium hydroxide solution (32 per cent strength by weight) were added
  4. extractionthe mixture was then extracted twice with 250 ml of a mixture of equal volumes of tetrahydrofuran and ethyl acetate each time
  5. dry with materialthe combined extracts were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated
  8. customThe crude product obtained (48.9 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-5bfe5bce30da4293805e6878c441d33c
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384961B2

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