Diethylamine → HCID 23459457, compound

HRID 2287133Notes

Reaction equation

HRID 2287133 reaction equation
[C:1]1([C:7]2([CH:13]([CH3:20])[CH2:14]OS(C)(=O)=O)[CH:12]=[CH:11][CH2:10][CH:9]=[CH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:21]([NH:23][CH2:24][CH3:25])[CH3:22]>C1(C)C=CC=CC=1>[CH3:20][CH:13]([C:7]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:12]=[CH:11][CH2:10][CH:9]=[CH:8]1)[CH2:14][N:23]([CH2:24][CH3:25])[CH2:21][CH3:22]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 54425854HCID 54425854, compound

Product 1

HCID 23459457HCID 23459457, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

8 g. of methanesulfonic acid 2-(1-phenyl-2,5-cyclohexadien-1-yl)-propyl ester are dissolved in 10 ml. of toluene. 8.4 ml. (about 3 equivalents) of condensed diethylamine are added at -10° C. The mixture is subsequently held at 150° C. in a pressure vessel for 25 hours. After cooling, the toluene phases is washed with water, concentrated, treated with ether and 3 N aqueous hydrochloric acid and extracted. The aqueous phase is made basic with concentrated aqueous ammonia and extracted with ether. The combined ether phases are dried over sodium sulfate, filtered and concentrated completely. There is obtained an oily product which is chromatographed on silica gel with methylene chloride/methanol (10:1). There is obtained β-methyl-N,N-diethyl-1-phenyl-2,5-cyclohexadien-1-ethylamine as an oily product. This product is converted as usual into the hydrochloride which, after recrystallization from ethanol/ether, has a melting point of 132°-137° C.

Workup

  1. additionare added at -10° C
  2. temperatureAfter cooling
  3. washthe toluene phases is washed with water
  4. concentrationconcentrated
  5. additiontreated with ether and 3 N aqueous hydrochloric acid
  6. extractionextracted
  7. extractionextracted with ether
  8. dry with materialThe combined ether phases are dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated completely
  11. customThere is obtained an oily product which
  12. customis chromatographed on silica gel with methylene chloride/methanol (10:1)

Sources & evidence

ORD record
ord-f9ec7477cc1c4c8683c70da6467a5a3a
Source dataset
uspto-grants-1981_05
Patent number
US04269788

Reaction notes

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