4-((4-Chlorophenyl)-2-pyridinylmethoxy)-1-piperidinebutanoic Acid → HCID 19753218, compound

HRID 483603

Reaction equation

HRID 483603 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)[O:9][CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][C:19](O)=[O:20])[CH2:12][CH2:11]2)=[CH:4][CH:3]=1.C1(N=C=NC2CCCCC2)CCCCC1.[NH2:43][C:44]1[CH:45]=[C:46]([O:59][CH3:60])[CH:47]=[C:48]2[C:53]=1[O:52][C:51]([C:54]([O:56][CH3:57])=[O:55])=[CH:50][C:49]2=[O:58]>ClCCl>[CH3:60][O:59][C:46]1[CH:47]=[C:48]2[C:53](=[C:44]([NH:43][C:19]([CH2:18][CH2:17][CH2:16][N:13]3[CH2:14][CH2:15][CH:10]([O:9][CH:8]([C:5]4[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=4)[C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=4)[CH2:11][CH2:12]3)=[O:20])[CH:45]=1)[O:52][C:51]([C:54]([O:56][CH3:57])=[O:55])=[CH:50][C:49]2=[O:58]

Participants

5

Reactant 3

HCID 23504-((4-Chlorophenyl)-2-pyridinylmethoxy)-1-piperidinebutanoic AcidHCID 10868DicyclohexylcarbodiimideHCID 19753201HCID 19753201, compound

Product 1

HCID 19753218HCID 19753218, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To 2.0 g (5.14 mmol) of 4-(4-[(4-chlorophenyl)-2-pyridylmethoxy]piperidinyl)butanoic acid dissolved in 20 ml of dichloromethane was added 1.27 g (6.17 mmol) of dicyclohexylcarbodiimide, and the mixture was stirred at 0° C. for 30 minutes. To the reaction mixture was added 1.54 g (6.18 mmol) of 8-amino-6-methoxy-2-methoxycarbonylchromone, and the mixture was further stirred at 0° C. for 3 hours. The reaction mixture was allowed to stand at room temperature overnight and then concentrated under reduced pressure. To the residue was added ethyl acetate, and the insolubles were filtered off. The filtrate was concentrated under reduced pressure, and the residue was applied to silica gel column chromatography using a mixed solvent of chloroform and methanol in a volume ratio of 20:1 as an eluent to obtain 0.50 g (yield: 17%) of 1-(3-[N-(6-methoxy-2-methoxycarbonylchromon-8-yl)carbamoyl]propyl)-4-[(4-chlorophenyl)-2-pyridylmethoxy]piperidine as a brown foamy product.

Workup

  1. stirringthe mixture was further stirred at 0° C. for 3 hours
  2. waitto stand at room temperature overnight
  3. concentrationconcentrated under reduced pressure
  4. additionTo the residue was added ethyl acetate
  5. filtrationthe insolubles were filtered off
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-bc54ac19e4654937b16cb4194689c3c2
Source dataset
uspto-grants-1993_07
Patent number
US05225559

Linked notes

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