Pyridine → HCID 13534239, compound

HRID 464431Notes

Reaction equation

HRID 464431 reaction equation
[O:1]([CH:8]1[CH2:12][CH2:11][N:10]([C:13](Cl)=[O:14])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH3:22][N:23]([CH3:27])[CH2:24][CH2:25][NH2:26]>O1CCCC1>[CH3:22][N:23]([CH3:27])[CH2:24][CH2:25][NH:26][C:13]([N:10]1[CH2:11][CH2:12][CH:8]([O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:9]1)=[O:14]

Participants

5

Reactant 3

HCID 1049PyridineHCID 66053N,N-DimethylethylenediamineHCID 20262995HCID 20262995, compound

Product 1

HCID 13534239HCID 13534239, compoundYield 16.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 0.088 mole of crude 3-phenoxy-1-pyrrolidinecarbonyl chloride in 100 ml of tetrahydrofuran was cooled to 0° C., treated with 7 g (0.088 mole) of pyridine (to remove any benzyl chloride contaminant), warmed to ambient temperature (1 hr.) and treated with 15.5 g (0.176 mole) of N,N-dimethylethylenediamine at a rapid drop rate. The reaction was slightly exothermic and after 2 hours, the mixture was filtered to remove a fine silvery precipitate (hydrochloride of the diamine) and concentrated in vacuo to a dark oil. The oil was partitioned between isopropyl ether and water, the isopropyl ether phase separated and the aqueous portion extracted with 100 ml of isopropyl ether. The isopropyl ether extracts were combined and concentrated in vacuo to give an amber oil, 5 g. The aqueous phase was extracted with 3×50 ml of benzene, the extracts combined, washed with 20 ml of water, dried over magnesium sulfate and concentrated in vacuo to a dark oil, 12 g. This residue partially crystallized overnight and was recrystallized 2 times with charcoal treatment, first from isopropyl ether/ligroin, then from isopropyl ether (cooled in a refrigerator) to give 4.1 g of white crystalline product which after drying at 64° C. under reduced pressure for 18 hours weighed 3.9 g, m.p. 72°-73° C. The residue from the original isopropyl extracts (5 g) was combined with the filtrate from above and upon reworking, gave an additional 4.3 g of product, m.p. 71°-73° C. The fraction with m.p. 72°-73° C. was submitted for elemental analysis and testing.

Workup

  1. customto remove any benzyl chloride contaminant),
  2. filtrationthe mixture was filtered
  3. customto remove a fine silvery precipitate (hydrochloride of the diamine) and
  4. concentrationconcentrated in vacuo to a dark oil
  5. customThe oil was partitioned between isopropyl ether and water
  6. customthe isopropyl ether phase separated
  7. extractionthe aqueous portion extracted with 100 ml of isopropyl ether
  8. concentrationconcentrated in vacuo
  9. customto give an amber oil, 5 g
  10. extractionThe aqueous phase was extracted with 3×50 ml of benzene
  11. washwashed with 20 ml of water
  12. dry with materialdried over magnesium sulfate
  13. concentrationconcentrated in vacuo to a dark oil, 12 g
  14. customThis residue partially crystallized overnight and was recrystallized 2 times with charcoal treatment
  15. temperaturefirst from isopropyl ether/ligroin, then from isopropyl ether (cooled in a refrigerator)

Sources & evidence

ORD record
ord-48b5af5beb0742cfb2c7065d2c0e4d44
Source dataset
uspto-grants-1985_10
Patent number
US04547514

Reaction notes

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