Sodium Carbonate → HCID 67493937, compound

HRID 408639Notes

Reaction equation

HRID 408639 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[C:7]1[N:12]=[CH:11][C:10]([C:13]23[CH2:19][N:16]([CH2:17][CH2:18]2)[CH2:15][CH2:14]3)=[CH:9][CH:8]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.ClCCl>[N:1]1([C:7]2[N:12]=[CH:11][C:10]([C:13]34[CH2:19][N:16]([CH2:15][CH2:14]3)[CH2:17][CH2:18]4)=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 31268PyrrolidineHCID 59187099HCID 59187099, compound

Product 1

HCID 67493937HCID 67493937, compoundYield 41.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
130 °C

Procedure

0.852 g (11.98 mmol) of pyrrolidine is added to a sealed tube comprising 0.060 g (0.29 mmol) of 4-(6-chloropyridin-3-yl)-1-azabicyclo[2.2.1]heptane obtained in stage 5.1 of Example 5. The mixture is heated at 130° C. for 3 hours, cooled to ambient temperature and diluted with 40 ml of toluene and the combined mixture is concentrated under reduced pressure. The residue thus obtained is diluted with 50 ml of dichloromethane and poured into 300 ml of a saturated aqueous sodium carbonate solution. The aqueous phase is extracted twice with 100 ml of dichloromethane, and the combined organic phases are dried over sodium sulfate and concentrated under reduced pressure. The residue is purified by chromatography on a column of silica gel, elution being carried out with a mixture of chloroform, methanol and aqueous ammonia in the proportions 85/15/1.5. 0.029 g of the expected product is obtained in the form of a brown powder.

Workup

  1. temperaturecooled to ambient temperature
  2. concentrationthe combined mixture is concentrated under reduced pressure
  3. customThe residue thus obtained
  4. extractionThe aqueous phase is extracted twice with 100 ml of dichloromethane
  5. dry with materialthe combined organic phases are dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by chromatography on a column of silica gel, elution
  8. additionbeing carried out with a mixture of chloroform, methanol and aqueous ammonia in the proportions 85/15/1.5

Sources & evidence

ORD record
ord-c22904a9bbf24937a747a07902e4d744
Source dataset
uspto-grants-2014_06
Patent number
US08759343B2

Reaction notes

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