Acetic Acid → 1-(4-(4-((Cyclobutylamino)methyl)-3-fluorophenyl)piperazin-1-yl)ethanone

HRID 1505601노트

반응식

HRID 1505601 반응식
[CH:1]1([NH2:5])[CH2:4][CH2:3][CH2:2]1.[C:6]([N:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:22]=[CH:21][C:18]([CH:19]=O)=[C:17]([F:23])[CH:16]=2)[CH2:11][CH2:10]1)(=[O:8])[CH3:7].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.[OH-].[Na+]>ClC(Cl)C>[CH:1]1([NH:5][CH2:19][C:18]2[CH:21]=[CH:22][C:15]([N:12]3[CH2:11][CH2:10][N:9]([C:6](=[O:8])[CH3:7])[CH2:14][CH2:13]3)=[CH:16][C:17]=2[F:23])[CH2:4][CH2:3][CH2:2]1

참가 물질

7

반응물 5

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 75645CyclobutylamineHCID 5049666Sodium triacetoxyborohydrideHCID 866906364-(4-Acetylpiperazin-1-yl)-2-fluorobenzaldehyde

생성물 1

HCID 866906371-(4-(4-((Cyclobutylamino)methyl)-3-fluorophenyl)piperazin-1-yl)ethanone수율 106%

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

To a solution of cyclobutanamine (1.26 mL, 14.7 mmol) and 4-(4-acetylpiperazin-1-yl)-2-fluoro-benzaldehyde (3.68 g, 14.7 mmol) in dichloroethane (50 mL) was added sodium triacetoxyborohydride (4.39 g, 20.6 mmol) followed by acetic acid (0.84 mL, 14.7 mmol) and the reaction was stirred at ambient temperature for 16 hours. 1 N aqueous NaOH was then added to basify the reaction and the product was extracted with Et2O (×3), washed with brine, dried with MgSO4, concentrated and dried in vacuo to give 1-[4-[4-[(cyclobutylamino)methyl]-3-fluoro-phenyl]piperazin-1-yl]ethanone (4.76 g, 99% yield). The product was used without purification. LCMS (m/z) ES+ 306 [M+1]+.

후처리

  1. customthe reaction
  2. extractionthe product was extracted with Et2O (×3)
  3. washwashed with brine
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated
  6. customdried in vacuo

출처 및 근거

ORD 기록
ord-eaae8134f5d344a7b7fce6097420d778
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216988B2

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