1-Methylpiperazine → HCID 131723007, compound

HRID 2268534Notes

Reaction equation

HRID 2268534 reaction equation
[CH3:1][O:2][C:3]1[C:4](=[O:29])[C:5]2[CH2:6][CH:7]([CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]3[CH:28]=[CH:27][C:23]([C:24]([OH:26])=O)=[CH:22][CH:21]=3)[CH2:8][C:9]=2[C:10](=[O:14])[C:11]=1[O:12][CH3:13].[CH3:30][N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1.Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1>O.C(N(CC)CC)C>[CH3:13][O:12][C:11]1[C:10](=[O:14])[C:9]2[CH2:8][CH:7]([CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]3[CH:21]=[CH:22][C:23]([C:24]([N:34]4[CH2:35][CH2:36][N:31]([CH3:30])[CH2:32][CH2:33]4)=[O:26])=[CH:27][CH:28]=3)[CH2:6][C:5]=2[C:4](=[O:29])[C:3]=1[O:2][CH3:1]

Participants

7

Reactant 4

HCID 531671-MethylpiperazineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 18348629HCID 18348629, compound

Product 1

HCID 131723007HCID 131723007, compoundYield 49.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 4-[4-(5,6-dimethoxy-4,7-dioxoindan-2-yl)butoxy]benzoic acid (500 mg), 1-methylpiperazine (250 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (479 mg), 1-hydroxybenzotriazole monohydrate (383 mg), triethylamine (0.697 ml), andTHF (20 ml) was stirred at room temperature for 10 hr. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride and dried. The solvent was removed in vacuo. The residue was purified by alumina column chromatography (ethyl acetate) and then with recrystallization from ethyl acetate-diisopropylether to yield the entitled compound (297 mg) as crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated aqueous sodium chloride
  3. customdried
  4. customThe solvent was removed in vacuo
  5. customThe residue was purified by alumina column chromatography (ethyl acetate)
  6. customwith recrystallization from ethyl acetate-diisopropylether

Sources & evidence

ORD record
ord-8c8bbb5bd7884fa8863c763204db3211
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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