Chloroform → HCID 23150261, compound

HRID 657640Notes

Reaction equation

HRID 657640 reaction equation
[N:1]1([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14](C3(C(O)=O)C=CC=CC3)=[CH:13][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:26](Cl)(=[O:30])[C:27](Cl)=O.C(Cl)(Cl)Cl.[NH:36]1[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1>ClCCl.CN(C)C=O>[N:36]1([C:26]([C:27]2[CH:6]=[CH:5][C:4]([C:14]3[CH:15]=[CH:16][C:11]([O:10][CH2:9][CH2:8][CH2:7][N:1]4[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]4)=[CH:12][CH:13]=3)=[CH:3][CH:2]=2)=[O:30])[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1

Participants

8

Reactant 4

HCID 6212ChloroformHCID 8082PiperidineHCID 65578Oxalyl chlorideHCID 23150275HCID 23150275, compound

Product 1

HCID 23150261HCID 23150261, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4′-(3-piperidinopropoxy)biphenyl-1-carboxylic acid (0.9 g) in dichloromethane (10 mL) containing one drop of N,N-dimethylformamide is added oxalyl chloride (285 μL). The suspension is stirred for one hour at room temperature, then chloroform (20 mL) and a drop of N,N-dimethylformamide are added. and the mixture is stirred for three hours at room temperature. Piperidine (1.6 mL) is then added and the mixture is stirred for an half hour at room temperature, washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The product thus obtained is purified by chromatography over silica gel with a gradient dichloromethane/methanol from 100/0 to 90/10. Fraction containing the expected product are pooled, concentrated under reduced pressure to give 620 mg of 1-(3-{[4′-(piperidinocarbonyl)biphenyl-4-yl]oxy}propyl)-piperidine as white crystals melting at 122° C.

Workup

  1. stirringand the mixture is stirred for three hours at room temperature
  2. stirringthe mixture is stirred for an half hour at room temperature
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe product thus obtained
  7. customis purified by chromatography over silica gel with a gradient dichloromethane/methanol from 100/0 to 90/10
  8. additionFraction containing the expected product
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a5e5b45c9ba34dc188614fed832e68bd
Source dataset
uspto-grants-2011_12
Patent number
US08076329B2

Reaction notes

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