1-Hydroxybenzotriazole → HCID 21937019, compound

HRID 1241899Notes

Reaction equation

HRID 1241899 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][C:13]([OH:15])=O)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].Cl.Cl.[NH2:18][CH:19]1[CH2:24][CH2:23][N:22]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([Cl:33])[CH:27]=2)[CH2:21][CH2:20]1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.C(N(CC)CC)C>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([O:10][CH2:11][CH2:12][C:13]([NH:18][CH:19]2[CH2:24][CH2:23][N:22]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([Cl:33])[CH:27]=3)[CH2:21][CH2:20]2)=[O:15])=[CH:8][CH:9]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 8199223-(4-acetylphenoxy)propanoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 219371291-(3,4-Dichlorobenzyl)piperidin-4-ylamine dihydrochloride

Product 1

HCID 21937019HCID 21937019, compoundYield 60.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

3-(4-Acetylphenyloxy)propionic acid (1.0 g) and 4-amino-1-(3,4-dichlorobenzyl)piperidine dihydrochloride (1.6 g) were suspended in DMF (50 mL), and triethylamine (1.3 mL), EDC hydrochloride (1.1 g) and HOBt (0.9 g) were added to the suspension. The suspension was stirred for 12 hrs. The reaction mixture was washed with water and then saturated brine and dried, and the solvent was evaporated under reduced pressure. Diisopropyl ether was added to the residue to crystallize to give the title compound (1.3 g) as a white solid.

Workup

  1. washThe reaction mixture was washed with water
  2. dry with materialsaturated brine and dried
  3. customthe solvent was evaporated under reduced pressure
  4. additionDiisopropyl ether was added to the residue
  5. customto crystallize

Sources & evidence

ORD record
ord-85e349c8dc1149d493e2e7c734ac338e
Source dataset
uspto-grants-2006_10
Patent number
US07115635B2

Reaction notes

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