Hydrochloric Acid → HCID 23458691, compound

HRID 1679952Notes

Reaction equation

HRID 1679952 reaction equation
[I-].[F:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:16])[CH2:10]C[N+](C)(C)C)=[CH:5][CH:4]=1.[ClH:17].[CH3:18][NH:19][CH3:20].Cl.FC1C=CC(C(=O)C)=CC=1>C(O)C.C(OCC)C>[ClH:17].[CH3:18][N:19]([CH3:20])[CH2:10][C:9]([C:6]1[CH:5]=[CH:4][C:3]([F:2])=[CH:8][CH:7]=1)=[O:16]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 98284'-FluoroacetophenoneHCID 10473Dimethylamine, hydrochlorideHCID 23458693HCID 23458693, compoundHCID 178486302HCID 178486302, compound2×

Product 1

HCID 23458691HCID 23458691, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
20 °C

Procedure

3-(4-Fluorophenyl)-3-oxo-N,N,N-trimethylpropan-1-aminium iodide can be prepared in accordance with the following procedure: Dimethylamine hydrochloride (32.6 g), a 12 N aqueous solution of hydrochloric acid (1 cc) and polyoxymethylene (12.0 g) are added to a solution of 1-(4-fluorophenyl)-ethanone (56.0 g) in ethanol (200 cc). After heating under reflux for 3 hours, more polyoxymethylene (6.0 g) is added and the mixture is heated under reflux for a further 16 hours. The reaction mixture is cooled to 20° C. and diethyl ether (300 cc) is then added. The solid which precipitates is filtered off, washed 3 times with diethyl ether (300 cc in total) and dried under reduced pressure (20 mm Hg) at 25° C. for 16 hours. 2-Dimethylamino-1-(4-fluorophenyl)-ethan-1-one hydrochloride (65.0 g), which melts at 180° C., is thus obtained and this is dissolved in distilled water (60 cc). Diethyl ether (1,100 cc) and a 10 N aqueous solution of sodium hydroxide (30 cc) are added to the solution thus obtained, the mixture is stirred for 2 minutes and the organic phase is decanted. The aqueous phase is re-extracted twice with diethyl ether (300 cc in total). The ether extracts are combined, dried over sodium sulphate and evaporated under reduced pressure (20 mm Hg) at 40° C. Methyl iodide (42.5 g) is added, at between 20° and a maximum of 50° C., to a solution of the residual oil (52.2 g) in anhydrous acetonitrile (250 cc). The reaction is allowed to proceed for 2 hours at 20° C. and diethyl ether (300 cc) is then added. The solid which precipitates is filtered off, washed 3 times with diethyl ether (300 cc in total), and dried under reduced pressure (20 mm Hg) at 25° C. for 16 hours. 3-(4-Fluorophenyl)-3-oxo-N,N,N-trimethylpropan-1-aminium iodide (65.5 g), which melts at 230° C., is thus obtained.

Workup

  1. temperatureAfter heating
  2. temperatureunder reflux for 3 hours
  3. temperaturethe mixture is heated
  4. temperatureunder reflux for a further 16 hours
  5. customThe solid which precipitates
  6. filtrationis filtered off
  7. washwashed 3 times with diethyl ether (300 cc in total)
  8. customdried under reduced pressure (20 mm Hg) at 25° C. for 16 hours

Sources & evidence

ORD record
ord-953c86ea172e487e92671a81d23c15b2
Source dataset
uspto-grants-1981_06
Patent number
US04271167

Reaction notes

Loading…