1,4'-Bipiperidine → 4,5,6,7-Tetramethoxy-2-[3-[4-[(4-piperidinopiperidino)carbonyl]phenoxy]propyl]indan hydrochloride

HRID 2268488Notes

Reaction equation

HRID 2268488 reaction equation
[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[C:9]([O:16][CH3:17])=[C:8]2[C:4]=1[CH2:5][CH:6]([CH2:18][CH2:19][CH2:20][O:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([OH:28])=O)=[CH:24][CH:23]=1)[CH2:7]2.[N:31]1([CH:37]2[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]2)[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1.[ClH:43].C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1>C1COCC1.O.C(N(CC)CC)C>[ClH:43].[CH3:17][O:16][C:9]1[C:10]([O:14][CH3:15])=[C:11]([O:12][CH3:13])[C:3]([O:2][CH3:1])=[C:4]2[C:8]=1[CH2:7][CH:6]([CH2:18][CH2:19][CH2:20][O:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([N:40]3[CH2:41][CH2:42][CH:37]([N:31]4[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]4)[CH2:38][CH2:39]3)=[O:28])=[CH:24][CH:23]=1)[CH2:5]2

Participants

8

Reactant 4

HCID 786071,4'-BipiperidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 183485514-[3-(4,5,6,7-Tetramethoxyindan-2-yl)propoxy]benzoic acid

Product 1

HCID 183485344,5,6,7-Tetramethoxy-2-[3-[4-[(4-piperidinopiperidino)carbonyl]phenoxy]propyl]indan hydrochlorideYield 98.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

The mixture of 4-[3-(4,5,6,7-tetramethoxyindan-2-yl)propoxy]benzoic acid (2.00 g), 4-piperidinopiperidine (1.62 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.84 g), 1-hydroxybenzotriazole monohydrate (1.47 g), and triethylamine (2.01 ml) in THF (40 ml) was stirred at room temperature for 12 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 (hexane to hexane:ethyl acetate=1:2) and converted into its hydrochloride, which was further recrystallized from ethanol-diisopropylether to yield the entitled compound (2.85 g) 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 (hexane to hexane:ethyl acetate=1:2)
  6. customwas further recrystallized from ethanol-diisopropylether

Sources & evidence

ORD record
ord-c62c12c3c1c245c7af11574d0b567a5d
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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