Methyl 4-fluorobenzoate → Methyl 4-(4-methyl-1,4-diazepan-1-yl)benzoate

HRID 16867

반응식

HRID 16867 반응식
[CH3:1][N:2]1[CH2:8][CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.F[C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=1>CC(N(C)C)=O>[CH3:1][N:2]1[CH2:8][CH2:7][CH2:6][N:5]([C:10]2[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=2)[CH2:4][CH2:3]1

참가 물질

4

반응물 2

HCID 67878Methyl 4-fluorobenzoateHCID 2283491-Methylhomopiperazine

생성물 1

HCID 66589865Methyl 4-(4-methyl-1,4-diazepan-1-yl)benzoate수율 24.1%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

반응 조건

온도
100 °C

실험 절차

1-Methyl-1,4-diazepane (15.07 g, 132.00 mmol) was added to methyl 4-fluorobenzoate (7.76 mL, 60 mmol) in DMA (150 mL). The resulting solution was stirred at 100° C. for 40 h. The reaction mixture was evaporated and quenched with 2M sodium hydroxide (50 ml). This was extracted with DCM (3×50 ml). The combined organic extracts were washed with saturated brine (50 ml), dried over MgSO4, filtered and evaporated to dryness. The crude product was purified by silica column chromatography, eluting with a gradient of 0 to 10% MeOH in DCM. Pure fractions were evaporated to dryness to afford methyl 4-(4-methyl-1,4-diazepan-1-yl)benzoate (3.59 g, 24.10%) as a tan waxy solid.

후처리

  1. customThe reaction mixture was evaporated
  2. customquenched with 2M sodium hydroxide (50 ml)
  3. extractionThis was extracted with DCM (3×50 ml)
  4. washThe combined organic extracts were washed with saturated brine (50 ml)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe crude product was purified by silica column chromatography
  9. washeluting with a gradient of 0 to 10% MeOH in DCM
  10. customPure fractions were evaporated to dryness

출처 및 근거

ORD 기록
ord-71297f6e18f245419f536eb64c14b8be
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737149B2

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