Potassium Carbonate → HCID 15941902, compound

HRID 657642Notes

Reaction equation

HRID 657642 reaction equation
C(=O)([O-])[O-].[K+].[K+].S(O[CH2:18][CH2:19][C:20]#[C:21][C:22]1[CH:37]=[CH:36][C:25]([O:26][CH2:27][CH2:28][CH2:29][N:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)=[CH:24][CH:23]=1)(C1C=CC(C)=CC=1)(=O)=O>N1CCCCC1.C(#N)C>[N:30]1([CH2:18][CH2:19][C:20]#[C:21][C:22]2[CH:23]=[CH:24][C:25]([O:26][CH2:27][CH2:28][CH2:29][N:30]3[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]3)=[CH:36][CH:37]=2)[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 23150320HCID 23150320, compound

Product 1

HCID 15941902HCID 15941902, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8082PiperidineSolvent

Procedure

A suspension of potassium carbonate (760 mg) in a solution of 1-{3-[4-(4-tosyloxybut-1-yn-1-yl)phenoxy]propyl}piperidine (487 mg) in a mixture of piperidine (1.09 mL) and acetonitrile (8 mL) is heated at a temperature close to 60° C. for 24 h. The suspension is filtrated. The filtrate concentrated under reduced pressure and purified by chromatography over silica gel using a gradient dichloromethane/methanol from 100/0 to 95/5. Fraction containing the expected product are pooled, concentrated under reduced pressure and salted with oxalic acid to give 190 mg of 1-{3-[4-(4-piperidinobut-1-yn-1-yl)phenoxy]propyl}piperidine as an off white solid melting at 167° C.

Workup

  1. temperatureis heated at a temperature
  2. customclose to 60° C. for 24 h
  3. filtrationThe suspension is filtrated
  4. concentrationThe filtrate concentrated under reduced pressure
  5. custompurified by chromatography over silica gel using a gradient dichloromethane/methanol from 100/0 to 95/5
  6. additionFraction containing the expected product
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-45849274a15a4e978a1891e6be5a03f2
Source dataset
uspto-grants-2011_12
Patent number
US08076329B2

Reaction notes

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