Water → HCID 20262978, compound

HRID 464433Notes

Reaction equation

HRID 464433 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[O:5][CH:6]1[CH2:10][CH2:9][N:8]([C:11](Cl)=[O:12])[CH2:7]1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:23]([N:25]([CH2:30][CH3:31])[CH2:26][CH2:27][CH2:28][NH2:29])[CH3:24].O>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[O:5][CH:6]1[CH2:10][CH2:9][N:8]([C:11]([NH:29][CH2:28][CH2:27][CH2:26][N:25]([CH2:30][CH3:31])[CH2:23][CH3:24])=[O:12])[CH2:7]1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 61011N,N-Diethyl-1,3-propanediamineHCID 129995883-(3-Chlorophenoxy)pyrrolidine-1-carbonyl chloride

Product 1

HCID 20262978HCID 20262978, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A stirred solution, 13 g (0.05 mole) of 3-(3-chlorophenoxy)-1-pyrrolidinecarbonyl chloride in 100 ml of chloroform was treated with 25 mg of ice and 12.8 g of sodium carbonate after 5 min. This mixture was treated with 7.15 g (0.055 mole) of N,N-diethyl-1,3-propanediamine dropwise and allowed to stir for 78 hours. The reaction mixture was transferred to a separatory funnel and enough water was added to form two distinct phases. The organic phase (chloroform) was separated and washed with 50 ml of water; the organic portion was extracted with 50 ml of 3N hydrochloric acid, separated and washed with 2×25 ml of water. All the aqueous portions were combined and the pH adjusted to neutral with 3N sodium hydroxide and extracted with 4×30 ml of chloroform. The extract was combined, washed with water, dried over magnesium sulfate and concentrated on a rotary vacuum to a pale yellow oil (12 g). The oil was dissolved in chloroform, treated with 1.5 g of charcoal and filtered hot. This was then slurried with 25 g of silica gel and filtered. The chloroform was discarded and the silica gel washed with methanol to give, after concentrating, 4 g of pale yellow oil. This was dissolved in ethyl ether and filtered through celite.

Workup

  1. customThe reaction mixture was transferred to a separatory funnel
  2. customto form two distinct phases
  3. customThe organic phase (chloroform) was separated
  4. washwashed with 50 ml of water
  5. extractionthe organic portion was extracted with 50 ml of 3N hydrochloric acid
  6. customseparated
  7. washwashed with 2×25 ml of water
  8. extractionextracted with 4×30 ml of chloroform
  9. washwashed with water
  10. dry with materialdried over magnesium sulfate
  11. concentrationconcentrated on a rotary vacuum to a pale yellow oil (12 g)
  12. dissolutionThe oil was dissolved in chloroform
  13. additiontreated with 1.5 g of charcoal
  14. filtrationfiltered hot
  15. filtrationfiltered
  16. washthe silica gel washed with methanol
  17. customto give
  18. concentrationafter concentrating
  19. dissolutionThis was dissolved in ethyl ether
  20. filtrationfiltered through celite

Sources & evidence

ORD record
ord-57c7b267fa0140788a081307d7a944d1
Source dataset
uspto-grants-1985_10
Patent number
US04547514

Reaction notes

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