Diisopropylamine → HCID 23355033, 화합물

HRID 234613

반응식

HRID 234613 반응식
C([Li])CCC.CC(NC(C)C)C.CN1CCC(=[C:20]2[C:26]3[CH:27]=[CH:28][S:29][C:25]=3C=[CH:23][N:22]3[CH:30]=[N:31][N:32]=[C:21]23)CC1.[CH3:33][N:34]1[CH2:39][CH2:38][CH:37]([C:40]([O:42]CC)=O)[CH2:36][CH2:35]1>CCCCCC.O1CCCC1.O>[CH3:33][N:34]1[CH2:35][CH2:36][CH:37]([C:40]([C:23]2[N:32]([CH2:21][CH2:20][C:26]3[CH:27]=[CH:28][S:29][CH:25]=3)[N:31]=[CH:30][N:22]=2)=[O:42])[CH2:38][CH2:39]1

참가 물질

8

반응물 4

HCID 7912DiisopropylamineHCID 11062856Ethyl 1-methylpiperidine-4-carboxylateHCID 23355014HCID 23355014, 화합물HCID 178418339Butyllithium

생성물 1

HCID 23355033HCID 23355033, 화합물수율 41.1%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매3회HCID 8058Hexane용매

실험 절차

Butyllithium in hexane (192 ml) was added dropwise at -70° C. under nitrogen to a solution of N-(1-methylethyl)-2-propanamine (43.4 ml) in tetrahydrofuran (400 ml) and the mixture was stirred for 30 minutes. A solution of intermediate (1) (0.236 mol) in tetrahydrofuran (50 ml) was added dropwise and the mixture was stirrred at -70° C. for 1 hour. Ethyl 1-methyl-4-piperidinecarboxylate (0.284 mol) in tetrahydrofuran (50 ml) was added and after the addition was completed, the mixture was stirred at -70° C. for 1 hour. The mixture was brought slowly to room temperature. The mixture was poured into water and extracted with 1,1'-oxybisethane/dichloromethane. The organic layer was dried (MgSO4) and evaporated. The residue (64.3 g) was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH/NH4OH 96/4/0.1 to 90/10/0.1) (35-70 μm). The pure fractions were collected and evaporated, yielding 29.55 g (41% ) of (1-methyl-4-piperidinyl)[2-[2-(3-thienyl)ethyl]-2H-1,2,4-triazol-3-yl]methanone (interm. 3);

후처리

  1. waitthe mixture was stirrred at -70° C. for 1 hour
  2. additionafter the addition
  3. stirringthe mixture was stirred at -70° C. for 1 hour
  4. customwas brought slowly to room temperature
  5. extractionextracted with 1,1'-oxybisethane/dichloromethane
  6. dry with materialThe organic layer was dried (MgSO4)
  7. customevaporated
  8. customThe residue (64.3 g) was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH/NH4OH 96/4/0.1 to 90/10/0.1) (35-70 μm)
  9. customThe pure fractions were collected
  10. customevaporated

출처 및 근거

ORD 기록
ord-5abeff183bdb489aa5b0c0d089ae5186
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05595988

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