Water → 1-(3-Butynyl)-4-(4-chlorophenyl)piperidine

HRID 366509

반응식

HRID 366509 반응식
[C:1]([O-])(O)=O.[Na+].[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]2CCNCC2)=[CH:9][CH:8]=1.[C:20]([C:24]1C=C(C=CC=1C)S([O-])(=O)=O)#[C:21]CC.O.[CH3:36][N:37]([CH3:40])[CH:38]=O>>[CH2:36]([N:37]1[CH2:40][CH2:14][CH:13]([C:10]2[CH:9]=[CH:8][C:7]([Cl:6])=[CH:12][CH:11]=2)[CH2:1][CH2:38]1)[CH2:24][C:20]#[CH:21]

참가 물질

6

반응물 5

HCID 962WaterHCID 6228Dimethylformamide2회HCID 516892Sodium BicarbonateHCID 37327804-(4-Chlorobenzyl)piperidineHCID 184280043-Butynyltosylate

생성물 1

HCID 184279681-(3-Butynyl)-4-(4-chlorophenyl)piperidine

반응 조건

온도
0 °C

실험 절차

A suspension of NaHCO3 (4 g) and 4-[(4-chlorophenyl)methyl]piperidine (18 mmol) in dimethylformamide (DMF) (25 mL) is stirred under a N2 atm at 0° C., and treated dropwise with 3-butynyltosylate (20 mmol) as a solution in DMF (50 mL). The reaction mixture is heated at 80° C. and stirred an additional 18 hours. After cooling the reaction mixture is stirred vigorously with the addition of water (200 mL), and then extracted with ethyl acetate. The organic layer is dried over magnesium sulfate, filtered and evaporated. The residue is purified by silica gel column chromatography (100:1 CH2Cl2 :MeOH) to give 1-(3-butynyl)-4-(4-chlorophenyl)piperidine.

후처리

  1. temperatureThe reaction mixture is heated at 80° C.
  2. stirringstirred an additional 18 hours
  3. temperatureAfter cooling the reaction mixture
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer is dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is purified by silica gel column chromatography (100:1 CH2Cl2 :MeOH)

출처 및 근거

ORD 기록
ord-b4438eb1509d411faa60c37bf1570671
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06130234

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