Triethylamine → 4-(4-Isobutyrylpiperazine-1-carbonyl)benzaldehyde

HRID 1467549

반응식

HRID 1467549 반응식
[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1)=[O:2].C(N(CC)CC)C.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[CH3:41][CH:42]([CH3:51])[C:43]([N:45]1[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]1)=[O:44]>ClCCl>[C:43]([N:45]1[CH2:50][CH2:49][N:48]([C:7]([C:6]2[CH:5]=[CH:4][C:3]([CH:1]=[O:2])=[CH:11][CH:10]=2)=[O:9])[CH2:47][CH2:46]1)(=[O:44])[CH:42]([CH3:51])[CH3:41]

참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 120884-Formylbenzoic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27614092-Methyl-1-(piperazin-1-yl)propan-1-one

생성물 1

HCID 866390314-(4-Isobutyrylpiperazine-1-carbonyl)benzaldehyde수율 70%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a stirred mixture of 4-formylbenzoic acid (1.5 g, 10 mmol) in anhydrous dichloromethane (30 mL) was added triethylamine (2.52 g, 25 mmol), 1-hydroxybenzotriazole (1.5 g, 11 mmol), followed by 1-ethyl-3-(3-dimethylamino propyl)carbodiimide hydrochloride (2.1 g, 11 mmol). After the addition, the mixture was stirred at room temperature for 40 mins. Then the mixture was cooled to 0° C. and 2-methyl-1-(piperazin-1-yl)propan-1-one (2.12 g, 11 mmol) was added in portion-wise. After the addition, the mixture was allowed to stir at room temperature overnight. The mixture was diluted with dichloromethane (50 mL), washed with saturated citric acid (100 mL×2), followed by saturated sodium bicarbonate (100 mL×2), brine (50 mL), dried over anhydrous sodium sulfate, and concentrated to give 4-(4-isobutyrylpiperazine-1-carbonyl)benzaldehyde (2 g, yield 70%) as a light yellow oil. 1H-NMR (400 MHz, CDCl3) δ (ppm): 1.15 (d, 6H), 2.80 (brs, 1H), 3.39-3.80 (m, 8H), 7.58 (d, J=8.0 Hz, 1H), 7.95 (d, J=8.0 Hz, 1H), 10.07 (s, 1H); LC-MS (ESI) m/z: 289 (M+1)+.

후처리

  1. additionAfter the addition
  2. temperatureThen the mixture was cooled to 0° C.
  3. additionAfter the addition
  4. stirringto stir at room temperature overnight
  5. washwashed with saturated citric acid (100 mL×2)
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-3aa1c44e8f4b4aa6ad5aba1f80476008
출처 데이터셋
uspto-grants-2015_04
특허 번호
US08999987B2

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