Hydrochloric Acid → HCID 20263101, compound

HRID 464432Notes

Reaction equation

HRID 464432 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[Cl:17])[O:5][CH:6]1[CH2:10][CH2:9][N:8]([C:11]([NH2:13])=[O:12])[CH2:7]1.[CH3:18][N:19]([CH3:23])[CH2:20][CH2:21]N.Cl>O1CCCC1>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[Cl:17])[O:5][CH:6]1[CH2:10][CH2:9][N:8]([C:11]([NH:13][CH2:21][CH2:20][N:19]([CH3:23])[CH3:18])=[O:12])[CH2:7]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 66053N,N-DimethylethylenediamineHCID 20263092HCID 20263092, compound

Product 1

HCID 20263101HCID 20263101, compoundYield 40.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 17.7 g (0.06 mole) of 3-(3,4-dichlorophenoxy)-1-pyrrolidinecarboxamide in 170 ml of tetrahydrofuran was treated by the rapid addition of 10.6 g (0.12 mole) of N,N-dimethylethylenediamine. The reaction was slightly exothermic and the mixture was stirred at ambient temperature over the weekend. Filtration removed some precipitated diamine hydrochloride, and the filtrate was concentrated in vacuo to give an oil, 23 g. The oil was treated with ethereal hydrogen chloride to give a granular solid which was recrystallized twice from acetone to give 4.6 g of pale green product, m.p. 143°-145° C.

Workup

  1. filtrationFiltration
  2. customremoved some precipitated diamine hydrochloride
  3. concentrationthe filtrate was concentrated in vacuo
  4. customto give an oil, 23 g
  5. customto give a granular solid which
  6. customwas recrystallized twice from acetone

Sources & evidence

ORD record
ord-06185cae29144b3eb3007622c515af72
Source dataset
uspto-grants-1985_10
Patent number
US04547514

Reaction notes

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