Triethylamine → 3-(4-Isobutyrylpiperazine-1-carbonyl)benzaldehyde
Reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=O)=[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:6]([C:5]2[CH:4]=[C:3]([CH:11]=[CH:10][CH:9]=2)[CH:1]=[O:2])=[O:8])[CH2:47][CH2:46]1)(=[O:44])[CH:42]([CH3:51])[CH3:41]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 3-formylbenzoic acid (750 mg, 5 mmol) in anhydrous dichloromethane (15 mL) was added triethylamine (1.263 g, 12.5 mmol), 1-hydroxybenzotriazole (0.743 g, 5.5 mmol), followed by 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.05 g, 5.5 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 (1.06 g, 5.5 mmol) was added portionwise. After the addition, the mixture was stirred at room temperature overnight. The mixture was diluted with dichloromethane (50 mL), washed with saturated sodium bicarbonate (50 mL×2), 10% citric acid (50 mL), brine (30 mL), dried over anhydrous sodium sulfate, and concentrated to give 3-(4-isobutyrylpiperazine-1-carbonyl)benzaldehyde (1.44 g, yield: 95%) as a gum. LC-MS (ESI) m/z: 289(M+1)+.
Workup
- additionAfter the addition
- temperatureThen the mixture was cooled to 0° C.
- additionAfter the addition
- stirringthe mixture was stirred at room temperature overnight
- washwashed with saturated sodium bicarbonate (50 mL×2), 10% citric acid (50 mL), brine (30 mL)
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-12f36c656e56440ab0456af098414e88
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08012976B2
Reaction notes
Loading…