Methane → HCID 20190415, compound

HRID 1788762Notes

Reaction equation

HRID 1788762 reaction equation
Cl.Cl[C:3]([C:5]1[CH:6]=[C:7]([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[N:8]2[C:12]=1[CH2:11][CH2:10][CH2:9]2)=[O:4].CN.[C:21](#[N:23])C.C>C(Cl)Cl>[CH3:21][NH:23][C:3]([C:5]1[CH:6]=[C:7]([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[N:8]2[C:12]=1[CH2:11][CH2:10][CH2:9]2)=[O:4]

Participants

6

Reactant 4

HCID 297MethaneHCID 6329MethylamineHCID 6342AcetonitrileHCID 20190421HCID 20190421, compound

Product 1

HCID 20190415HCID 20190415, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

A suspension of 7-chloroformyl-5-(3-pyridyl)-2,3-dihydro-1H-pyrrolizine hydrochloride (14.1 g) in methylene chloride (250 cc) is saturated with a stream of anhydrous methylamine, while the temperature of the reaction mixture is kept at about 25° C. for 7 hours. The solution obtained is stirred at a temperature of about 20° C. for 16 hours and then methylene chloride (250 cc) and distilled water (250 cc) are added to it. The organic phase is separated, washed 3 times with distilled water (750 cc in total), dried over anhydrous magnesium sulphate, treated with decolourising charcoal (0.5 g), filtered and concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature of about 60° C. A crude product (12.2 g) melting at 184° 0 is thus obtained. This product is dissolved in boiling acetonitrile (150 cc). The solution obtained is treated with decolourising charcoal (0.5 g) and filtered hot. The filtrate is cooled at a temperature of about 4° C. for 1 hour. The crystals which have appeared are separated off by filtration, washed twice with acetonitrile (20 cc in total) cooled to a temperature of about 4° C. and 3 times with diethyl ether (75 cc in total), and then dried under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature of about 20° C. in the presence of potassium hydroxide pellets. N-methyl-5-(3-pyridyl)-2,3-dihydro-1H-pyrrolizine-7-carboxamide (7.1 g) is thus obtained in the form of cream crystals melting at 187° C.

Workup

  1. customThe solution obtained
  2. distillationmethylene chloride (250 cc) and distilled water (250 cc)
  3. additionare added to it
  4. customThe organic phase is separated
  5. washwashed 3 times with distilled water (750 cc in total)
  6. dry with materialdried over anhydrous magnesium sulphate
  7. additiontreated with decolourising charcoal (0.5 g)
  8. filtrationfiltered
  9. concentrationconcentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature of about 60° C
  10. customA crude product (12.2 g) melting at 184° 0 is thus obtained
  11. dissolutionThis product is dissolved
  12. customThe solution obtained
  13. filtrationfiltered hot
  14. temperatureThe filtrate is cooled at a temperature of about 4° C. for 1 hour
  15. customThe crystals which have appeared are separated off by filtration
  16. washwashed twice with acetonitrile (20 cc in total)
  17. temperaturecooled to a temperature of about 4° C. and 3 times with diethyl ether (75 cc in total)
  18. dry with materialdried under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature of about 20° C. in the presence of potassium hydroxide pellets

Sources & evidence

ORD record
ord-b36442ef1e0e427da9188dd8ef7623f7
Source dataset
uspto-grants-1987_08
Patent number
US04684658

Reaction notes

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