1-Isopropylpiperazine → 3-(4-Isopropylpiperazin-1-yl)benzaldehyde

HRID 922396노트

반응식

HRID 922396 반응식
Br[C:2]1[CH:3]=[C:4]([CH:8]2[O:13]CCCO2)[CH:5]=[CH:6][CH:7]=1.[CH:14]([N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)([CH3:16])[CH3:15].C(O[Na])(C)(C)C>C1(C)C=CC=CC=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[CH:14]([N:17]1[CH2:22][CH2:21][N:20]([C:2]2[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=2)[CH:8]=[O:13])[CH2:19][CH2:18]1)([CH3:16])[CH3:15]

참가 물질

6

반응물 3

HCID 780131-IsopropylpiperazineHCID 101058152-(3-Bromophenyl)-1,3-dioxaneHCID 178418730sodium 2-methylpropan-2-olate

생성물 1

HCID 840175373-(4-Isopropylpiperazin-1-yl)benzaldehyde수율 87.4%

시약·촉매·용매 2

HCID 634876Binap, (A+-)-촉매HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

A mixture of 2-(3-bromophenyl)-1,3-dioxane (2, 1.58 g, 6.5 mmol), 1-isopropylpiperazine (1.0 g, 7.8 mmol), rac-BINAP (60 mg, 0.096 mmol), and tert-BuONa (1.06 g, 11.1 mmol) in toluene (15 mL) was degassed under vacuum and flushed with nitrogen. Pd2(dba)3 (30 mg, 0.033. mmol) was added. The reaction mixture was degassed again and flushed with nitrogen and was heated at 100° C. under nitrogen for 16 h. The reaction mixture was poured into cold 1N HCl (30 mL) and stirred for 2 h. It was adjusted to pH 8 with 6N NaOH and extracted with EtOAc (3×50 mL). The combined organic layers were dried (MgSO4), filtered, concentrated, and purified by silica gel chromatography eluting with 0-100% EtOAc (containing 5% v/v Et3N) in hexanes to afford the title compound as a viscous yellow oil (1.32 g, 87%): 1H NMR (500 MHz, CDCl3) δ 9.96 (s, 1H), 7.44-7.37 (m, 2H), 7.34-7.30 (m, 1H), 7.21-7.16 (m, 1H), 3.28 (t, J=5.0 Hz, 4H), 2.73 (sept, J=6.5 Hz, 1H), 2.69 (t, J=5.0 Hz, 4H), 1.10 (d, J=6.5 Hz, 6H); ESI MS m/z 233 [M+H]+.

후처리

  1. customwas degassed under vacuum
  2. customflushed with nitrogen
  3. additionPd2(dba)3 (30 mg, 0.033. mmol) was added
  4. customThe reaction mixture was degassed again
  5. customflushed with nitrogen
  6. additionThe reaction mixture was poured into cold 1N HCl (30 mL)
  7. extractionextracted with EtOAc (3×50 mL)
  8. dry with materialThe combined organic layers were dried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. custompurified by silica gel chromatography
  12. washeluting with 0-100% EtOAc (
  13. additioncontaining 5% v/v Et3N) in hexanes

출처 및 근거

ORD 기록
ord-77d2d82a3b094e058024114599dc4902
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278940B2

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