1-Phenylpiperazine → HCID 18348553, compound

HRID 2268535Notes

Reaction equation

HRID 2268535 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](O)=[O:25])=[CH:22][CH:21]=3)[CH2:8][C:9]=2[C:10](=[O:14])[C:11]=1[O:12][CH3:13].[C:30]1(N2CCNCC2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.Cl.C(N=C=NCCCN(C)C)C.O.O[N:56]1[C:60]2C=[CH:62][CH:63]=[CH:64][C:59]=2N=N1>C1COCC1.O.C(N(CC)CC)C>[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:21]=[CH:22][C:23]([C:24]([N:56]4[CH2:62][CH2:63][CH:64]([C:30]5[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=5)[CH2:59][CH2:60]4)=[O:25])=[CH:27][CH:28]=3)[CH2:8][C:9]=2[C:10](=[O:14])[C:11]=1[O:12][CH3:13]

Participants

8

Reactant 4

HCID 70961-PhenylpiperazineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 18348629HCID 18348629, compound

Product 1

HCID 18348553HCID 18348553, compoundYield 58.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 4-[4-(5,6-dimethoxy-4,7-dioxoindan-2-yl)butoxy]benzoic acid (500 mg), 1-phenylpiperazine (406 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (479 mg), 1-hydroxybenzotriazole monohydrate (383 mg), triethylamine (0.697 ml) in THF (20 ml) was stirred at room temperature for 6 hr. The reaction mixture was diluted with water and extracted with combined solvent of THF and 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 recrystallized from THF-diisopropylether to yield the entitled compound (400 mg) as crystals.

Workup

  1. extractionextracted with combined solvent of THF and 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 recrystallized from THF-diisopropylether

Sources & evidence

ORD record
ord-1a98a45a259744c5a26df9193208d99a
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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