Sodium Azide → 2-((Dimethylamino)methyl)-1-(3-methoxyphenyl)cyclohexanol

HRID 363813ノート

反応式

HRID 363813 の反応式
[CH3:1][N:2]([CH2:4][CH:5]1[C:10]([OH:19])([C:11]2[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][CH:12]=2)[CH2:9][CH2:8][CH2:7][CH2:6]1)[CH3:3].Cl.[N-]=[N+]=[N-].[Na+]>FC(F)(F)C(O)=O>[CH3:3][N:2]([CH2:4][CH:5]1[C:10]([OH:19])([C:11]2[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][CH:12]=2)[CH2:9][CH2:8][CH2:7][CH2:6]1)[CH3:1]

参加物

4

反応物 2

HCID 33557Sodium AzideHCID 9971980Cyclohexanol, 2-((dimethylamino)methyl)-1-(3-methoxyphenyl)-, hydrochloride (1:1)

生成物 1

HCID 55232-((Dimethylamino)methyl)-1-(3-methoxyphenyl)cyclohexanol

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

実験手順

33.4 g of a mixture consisting of 45% (RR,SS) Tramadol hydrochloride and 55% of the corresponding (RS,SR) isomer was immersed in 50 ml trifluoroacetic acid, 5.2 g of sodium azide was added, and the reaction mixture was stirred for 24 hours. The reaction mixture was then evaporated under reduced pressure, 50 ml water was added, and the solution was brought to pH 12 with solid potassium carbonate. The suspension was extracted with 50 ml toluene, the solvent was evaporated and 25 ml hydrogen chloride solution in isopropanol were added. The solution was cooled and filtered. 9.5 g of crude (RR,SS) Tramadol were obtained, and the crude product was purified by recrystallization from isopropanol. The hitherto unknown (RS,SR)-2-(dimethylaminomethyl)-1-azido-1-(3-methoxyphenyl)-cyclohexane hydrochloride was isolated from the reaction mixture, recrystallized from isopropanol and characterized as follows:

後処理

  1. customThe reaction mixture was then evaporated under reduced pressure, 50 ml water
  2. additionwas added
  3. extractionThe suspension was extracted with 50 ml toluene
  4. customthe solvent was evaporated
  5. addition25 ml hydrogen chloride solution in isopropanol were added
  6. temperatureThe solution was cooled
  7. filtrationfiltered

出典と根拠

ORDレコード
ord-12f16a9f5c1441deada82670c4261a4a
出典データセット
uspto-grants-1999_02
特許番号
US05874620

反応ノート

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