Sodium Carbonate → HCID 69198981, compound

HRID 2251895Notes

Reaction equation

HRID 2251895 reaction equation
S(O[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[CH:10][CH:9]=1)(=O)(=O)C.[NH:20]1[CH2:26][CH2:25][CH2:24][C@@H:21]1[CH2:22][OH:23].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[OH:23][CH2:22][C@H:21]1[CH2:24][CH2:25][CH2:26][N:20]1[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 2724541Prolinol, (R)-HCID 22934161HCID 22934161, compound

Product 1

HCID 69198981HCID 69198981, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

4-Morpholinophenethyl mesylate (0.43 g, 1.51 mmol), D-prolinol (0.17 g, 1.66 mmol) and sodium carbonate (0.40 g, 2.89 mmol) were added to acetonitrile (20 ml), and they were stirred under heating at 70° C. overnight. The reaction mixture was cooled and then filtered. The filtrate was evaporated to dryness under reduced pressure, and the residue was distributed into water and ethyl acetate. The intended product was extracted from ethyl acetate layer with 1 M hydrochloric acid. The aqueous layer was neutralized and the product was again extracted with ethyl acetate. The organic layer was dried and the solvent was evaporated under reduced pressure to obtain (R)-2-hydroxymethyl-1-(4-morpholinophenethyl)pyrrolidine in the form of a light yellow solid (0.44 g, 1.5 mmol, 100%). This product was dissolved in dichloromethane (10 ml). Triethylamine (0.29 ml, 2.1 mmol) and methanesulfonyl chloride (0.15 ml, 1.9 mmol) were added to the obtained solution at 0° C., and they were stirred at room temperature for 1 hour. The reaction mixture was distributed into 5% aqueous sodium hydrogencarbonate solution and dichloromethane. The organic layer was dried and the solvent was evaporated under reduced pressure. The residue was subjected to the silica gel column chromatography. After the elution with hexane and ethyl acetate (1:1), suitable fractions were collected and the solvent was evaporated under reduced pressure to obtain (R)-3-chloro-1-(morpholinophenethyl)piperidine in the form of a white solid (0.30 g, 64%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. customThe filtrate was evaporated to dryness under reduced pressure
  4. extractionThe intended product was extracted from ethyl acetate layer with 1 M hydrochloric acid
  5. extractionthe product was again extracted with ethyl acetate
  6. customThe organic layer was dried
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-e3e1598a28ed451abff968314511a2cb
Source dataset
uspto-grants-2008_01
Patent number
US07320973B2

Reaction notes

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