4-Phenylbutyric Acid → 2,3-Dihydro-2,4,6,7-tetramethyl-2-[[4-(4-phenylbutyryl)-1-piperazinyl]methyl]-5-benzofuranamine

HRID 565691Notes

Reaction equation

HRID 565691 reaction equation
Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.[C:23]1([CH2:29][CH2:30][CH2:31][C:32]([OH:34])=O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[CH3:35][C:36]1([CH2:49][N:50]2[CH2:55][CH2:54][NH:53][CH2:52][CH2:51]2)[CH2:40][C:39]2[C:41]([CH3:48])=[C:42]([NH2:47])[C:43]([CH3:46])=[C:44]([CH3:45])[C:38]=2[O:37]1>CN(C)C=O.O>[CH3:35][C:36]1([CH2:49][N:50]2[CH2:55][CH2:54][N:53]([C:32](=[O:34])[CH2:31][CH2:30][CH2:29][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH2:52][CH2:51]2)[CH2:40][C:39]2[C:41]([CH3:48])=[C:42]([NH2:47])[C:43]([CH3:46])=[C:44]([CH3:45])[C:38]=2[O:37]1

Participants

7

Reactant 4

HCID 47754-Phenylbutyric AcidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 219977792,3-Dihydro-2,4,6,7-tetramethyl-2-[(1-piperazinyl)methyl]-5-benzofuranamine

Product 1

HCID 221109992,3-Dihydro-2,4,6,7-tetramethyl-2-[[4-(4-phenylbutyryl)-1-piperazinyl]methyl]-5-benzofuranamineYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.22 g) and 1-hydroxybenzotriazole (0.13 g) in N,N-dimethylformamide (5 mL) was added 0.12 g of 4-phenylbutyric acid at 0° C. and the mixture was stirred at that temperature for 5 minutes and further at room temperature for 2 hours. This reaction mixture was added to a solution of 2,3-dihydro-2,4,6,7-tetramethyl-2-[(1-piperazinyl)methyl]-5-benzofuranamine (0.20 g) in N,N-dimethylformamide (2 mL) at 0° C. and the mixture was further stirred for 30 minutes. This reaction mixture was poured into water and extracted with ethyl acetate. The extract was dried over MgSO4 and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1:2) to provide 0.22 g of the title compound. Yield 74%.

Workup

  1. stirringthe mixture was further stirred for 30 minutes
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried over MgSO4
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1:2)

Sources & evidence

ORD record
ord-fdc9b99e1bde4d169f7cc7fd95e2e23e
Source dataset
uspto-grants-2001_01
Patent number
US06172085B2

Reaction notes

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