Acetic Acid → 1-(4-Iodophenyl)-4-isopropylpiperazine

HRID 447328

반응식

HRID 447328 반응식
[I:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:14][C:15]([CH3:17])=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CC(O)=O>ClCCCl.C1COCC1>[I:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH:15]([CH3:17])[CH3:14])[CH2:10][CH2:9]2)=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 180AcetoneHCID 41478451-(4-Iodophenyl)piperazineHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 584861891-(4-Iodophenyl)-4-isopropylpiperazine수율 85%

시약·촉매·용매 1

HCID 21493386Dce thf용매

실험 절차

To a mixture of 1-(4-iodophenyl)piperazine (1.44 g, 5 mmol) and acetone (1.47 mL, 20 mmol) in DCE/THF (45 mL/15 mL) was added NaBH(OAc)3 (1.38 g, 6.5 mmol), followed by AcOH (0.5 mL). After addition, the resulting mixture was stirred O/N at rt. The reaction as quenched with sat. NaHCO3 (10 mL) and H2O (20 mL), and was then extracted with EtOAc (2×60 mL), dried over MgSO4 and concentrated to give the crude title compound as a light yellow solid (1.396 g, 85%). 1H NMR (400 MHz, DMSO-d6) δ 7.46 (d, J=8.4 Hz, 2H), 6.75 (d, J=8.8 Hz, 2H), 3.12-3.07 (m, 4H), 2.65 (p, J=6.5 Hz, 1H), 2.56-2.52 (m, 4H), 0.98 (d, J=6.4 Hz, 6H); MS ESI 330.9 [M+H]+, calcd. for [C13H19IN2+H]+ 331.1.

후처리

  1. additionAfter addition
  2. customThe reaction
  3. customas quenched with sat. NaHCO3 (10 mL) and H2O (20 mL)
  4. extractionwas then extracted with EtOAc (2×60 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-a053dac922eb49c79d0f718b45475a5e
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481533B2

연결된 노트

불러오는 중…