N,N-Dimethyl-1,3-propanediamine → HCID 13534236, compound

HRID 464430Notes

Reaction equation

HRID 464430 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+].[CH3:23][N:24]([CH3:29])[CH2:25][CH2:26][CH2:27][NH2:28]>C(Cl)(Cl)Cl.O>[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:28][CH2:27][CH2:26][CH2:25][N:24]([CH3:29])[CH3:23])=[O:12])[CH2:7]1

Participants

6

Reactant 3

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 10340Sodium CarbonateHCID 129995883-(3-Chlorophenoxy)pyrrolidine-1-carbonyl chloride

Product 1

HCID 13534236HCID 13534236, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

A solution, 13 g (0.05 mole) of 3-(3-chlorophenoxy)-1-pyrrolidinecarbonyl chloride in 100 ml of chloroform was stirred at 0° C. for 5 min. Then, the following were added in order: 25 g of ice, 12.8 g of sodium carbonate; and 5.62 g (0.055 mole) of N,N-dimethyl-1,3-propanediamine. The resulting mixture was allowed to come to room temperature and stirred for 72 hours. At this time the reaction mixture was diluted with excess water and the organic phase separated. The chloroform solution was washed with water and extracted with 50 ml of 3N hydrochloric acid. The chloroform portion was washed with 2×25 ml of water. The hydrochloric acid portion was combined with the last 2 washes and the pH adjusted to neutral with 3N sodium hydroxide. The resulting solution was extracted with 3×30 ml of chloroform and the chloroform extracts were combined, dried over magnesium sulfate and concentrated to a dark oil, 13.2 g. All of the samples were converted to the free base, charcoaled, and chromatographed on 25 g of silica gel. Elution with chloroform gave after concentrating a dark orange oil. Trituration of this oil with ethyl ether and concentration of the triturates gave 7 g of a pale yellow viscous oil. This oil was pumped under high vacuum for 24 hours. The oil upon standing crystallized and was recrystallized from ethyl ether/30-60 petroleum ether to give 3.2 g of fine white crystals; m.p. 60°-61° C.

Workup

  1. additionThen, the following were added in order
  2. customto come to room temperature
  3. customthe organic phase separated
  4. washThe chloroform solution was washed with water
  5. extractionextracted with 50 ml of 3N hydrochloric acid
  6. washThe chloroform portion was washed with 2×25 ml of water
  7. extractionThe resulting solution was extracted with 3×30 ml of chloroform
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated to a dark oil, 13.2 g
  10. customchromatographed on 25 g of silica gel
  11. washElution with chloroform
  12. customgave
  13. concentrationafter concentrating a dark orange oil

Sources & evidence

ORD record
ord-eea9c3e2f28749cdb52383037c373663
Source dataset
uspto-grants-1985_10
Patent number
US04547514

Reaction notes

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