Triethylamine → HCID 15907546, compound

HRID 459741Notes

Reaction equation

HRID 459741 reaction equation
C[N:2]1CCNCC1C1C=CC(N)=CC=1.O[C:16]1[C:24]2N=N[NH:21][C:20]=2[CH:19]=[CH:18][CH:17]=1.Cl.CN(C)CCCN=C=NCC.[CH2:37]([N:39]([CH2:42][CH3:43])[CH2:40][CH3:41])C.[N+:44]([C:47]1[CH:52]=[CH:51][C:50]([CH2:53][CH2:54][CH2:55][C:56]([OH:58])=O)=[CH:49][CH:48]=1)([O-:46])=[O:45]>ClCCl.O>[N+:44]([C:47]1[CH:52]=[CH:51][C:50]([CH2:53][CH2:54][CH2:55][C:56]([NH:2][C:17]2[CH:16]=[CH:24][C:20]([N:21]3[CH2:43][CH2:42][N:39]([CH3:37])[CH2:40][CH2:41]3)=[CH:19][CH:18]=2)=[O:58])=[CH:49][CH:48]=1)([O-:46])=[O:45]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 797114-(4-Nitrophenyl)butyric acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68579243HCID 68579243, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 15907546HCID 15907546, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

4-(N-methylpiperazinyl)aniline (0.5 g; 2.6 mmol), hydroxybenzotriazole (0.39 g; 2.86 mmol), 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (1.1 g; 5.7 mmol) and triethylamine (0.8 ml; 5.7 mmol) are added to a solution of 0.55 g (2.6 mmol) of 4-(4-nitrophenyl)butanoic acid in dichloromethane (30 ml). The reaction medium is stirred for 16 hours at ambient temperature, then the medium is diluted with 15 ml of water and the product is extracted with dichloromethane. The organic phase is dried over sodium sulphate followed by filtering and concentrating under vacuum and the residue is purified on a silica column (eluent: CH2Cl2/EtOH: 4/1). A clear oil is obtained with a yield of 84% (0.84 g).

Workup

  1. extractionthe product is extracted with dichloromethane
  2. dry with materialThe organic phase is dried over sodium sulphate
  3. filtrationby filtering
  4. concentrationconcentrating under vacuum
  5. customthe residue is purified on a silica column (eluent: CH2Cl2/EtOH: 4/1)
  6. customA clear oil is obtained with a yield of 84% (0.84 g)

Sources & evidence

ORD record
ord-b41610da23d04c1baa346187642f635e
Source dataset
uspto-grants-2007_03
Patent number
US07196084B2

Reaction notes

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