1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178481066, compound

HRID 1445149Notes

Reaction equation

HRID 1445149 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8](=[O:21])[CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=2)[CH:16]=O)[CH2:4][CH2:3]1.[CH:22]([C:24]1[CH:25]=C(C=C[CH:36]=1)OCCCC(O)=O)=O.CN1CCNCC1.CN(C)CCCN=C=NCC.O.O[N:57]1[C:61]2[CH:62]=[CH:63][CH:64]=[CH:65][C:60]=2[N:59]=N1>ClCCl.O>[C:24]([C:63]1[CH:64]=[CH:65][C:60]2[NH:59][C:16]([C:15]3[CH:14]=[C:13]([CH:20]=[CH:19][CH:18]=3)[O:12][CH2:11][CH2:10][CH2:9][C:8]([N:5]3[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]3)=[O:21])=[N:57][C:61]=2[CH:62]=1)([CH3:25])([CH3:36])[CH3:22]

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 531671-MethylpiperazineHCID 27960291-Hydroxybenzotriazole hydrateHCID 164956824-(3-Formylphenoxy)butanoic acidHCID 574809283-[4-(4-Methyl-piperazin-1-yl)-4-oxo-butoxy]-benzaldehyde

Product 1

HCID 178481066HCID 178481066, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

3-[4-(4-Methyl-piperazin-1-yl)-4-oxo-butoxy]-benzaldehyde. To a solution of 4-(3-formyl-phenoxy)-butyric acid (981 mg, 4.72 mmol, 1.0 equiv) and N-methylpiperazine (576 mg, 5.19 mmol, 1.1 equiv) in dichloromethane at 0° C. was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (EDCI; 1.18 g, 6.14 mmol, 1.3 equiv) and 1-hydroxybenzotriazole hydrate (HOBT; 701 mg, 5.19 mmol, 1.1 equiv). The reaction mixture, which was allowed to warm to rt, was stirred for 2.0 h and then poured into water. This mixture was extracted three times with ethyl acetate. The combined extracts were dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude residue was purified by column chromatography (silica gel, 5% MeOH in dichloromethane) to afford 847 mg (62%) of the desired product. 1H NMR (400 MHz, CD3OD): 9.72 (s, 1H), 7.29-7.23 (m, 2H), 7.22-7.19 (m, 1H), 7.05-6.98 (m, 1H), 3.87 (t, J=6.1 Hz, 2H), 3.43-3.31 (m, 4H), 2.39 (t, J=7.2 Hz, 2H), 2.27-2.17 (m, 4H), 2.08 (s, 3H), 1.92-1.80 (m, 2H).

Workup

  1. extractionThis mixture was extracted three times with ethyl acetate
  2. dry with materialThe combined extracts were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude residue was purified by column chromatography (silica gel, 5% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-a09bebdee49c40f08d4660c504734571
Source dataset
uspto-grants-2010_02
Patent number
US07662966B2

Reaction notes

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