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

HRID 2241733Notes

Reaction equation

HRID 2241733 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-c8694d45420d4e64916671b19d5b1b6b
Source dataset
uspto-grants-2010_05
Patent number
US07723526B2

Reaction notes

Loading…