Water → 4-(p-Chlorophenoxy)-2-methyl-1,2,3,4-tetrahydroisoquinoline hydrochloride

HRID 354558

반응식

HRID 354558 반응식
[CH3:1][N:2]1[CH2:11][CH:10]([OH:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3]1.[H-].[Na+].[Cl:15][C:16]1[CH:21]=[CH:20][C:19](F)=[CH:18][CH:17]=1.O>CN(C=O)C>[ClH:15].[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([O:12][CH:10]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH2:3][N:2]([CH3:1])[CH2:11]2)=[CH:18][CH:17]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 9604Benzene, 1-chloro-4-fluoro-HCID 24758Sodium hydrideHCID 125230552-Methyl-1,2,3,4-tetrahydro-4-isoquinolinol

생성물 1

HCID 131171004-(p-Chlorophenoxy)-2-methyl-1,2,3,4-tetrahydroisoquinoline hydrochloride수율 43.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
75 °C

실험 절차

A solution of 1,2,3,4-tetrahydro-2-methyl-4-isoquinolinol (3.3 g, 0.020 mole) in dry DMF is added dropwise under nitrogen to a suspension of sodium hydride 50% (98%) (1.6 g, 0.033 mole), previously washed with hexane, in 40 ml dry DMF, at 65° C. After the evolution of gas ceases, a solution of p-chlorofluorobenzene (3.6 g, 0.028 mole) in 15 ml dry DMF is added slowly, and the resulting mixture is allowed to stir at 75° C. for 16 hours. After cooling to room temperature the solution is poured into water (110 ml), extracted with chloroform, the chloroform phase is washed twice with water, dried (saturated NaCl, anhydrous MgSO4) and removed via reduced pressure to yield an oil which is purified by dry column chromatography, over silica gel using ethyl acetate as the eluent. The desired product is crystallized from ether as the hydrochloride salt, yielding 1.9 g (31%) of a solid of 4-(p-chlorophenoxy)-2-methyl-1,2,3,4-tetrahydroisoquinoline hydrochloride, d@92° C.

후처리

  1. washpreviously washed with hexane, in 40 ml dry DMF, at 65° C
  2. temperatureAfter cooling to room temperature the solution
  3. extractionextracted with chloroform
  4. washthe chloroform phase is washed twice with water
  5. dry with materialdried (saturated NaCl, anhydrous MgSO4)
  6. customremoved via reduced pressure
  7. customto yield an oil which
  8. customis purified
  9. customby dry column chromatography
  10. customThe desired product is crystallized from ether as the hydrochloride salt

출처 및 근거

ORD 기록
ord-898f06758fbf49bc8038568fa28e7378
출처 데이터셋
uspto-grants-1983_03
특허 번호
US04375471

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