Hydrochloric Acid → 3-Chloro-N,N-dimethyl-3-phenylpropan-1-amine--hydrogen chloride (1/1)

HRID 1248849Notes

Reaction equation

HRID 1248849 reaction equation
[CH3:1][N:2]([CH2:4][CH2:5][CH:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)O)[CH3:3].[ClH:14].S(Cl)([Cl:17])=O>C(Cl)(Cl)Cl>[ClH:17].[CH3:1][N:2]([CH2:4][CH2:5][CH:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[Cl:14])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 1106653-(Dimethylamino)-1-phenylpropan-1-ol

Product 1

HCID 127072403-Chloro-N,N-dimethyl-3-phenylpropan-1-amine--hydrogen chloride (1/1)

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution containing 442 g. of N,N-dimethyl 3-phenyl-3-hydroxypropylamine in 5 l. of chloroform was saturated with dry gaseous hydrogen chloride. 400 ml. of thionyl chloride were then added to the chloroform solution at a rate sufficient to maintain reflux. The solution was refluxed an additional 5 hours. Evaporation of the chloroform andd other volatile constituents in vacuo yielded N,N-dimethyl 3-phenyl-3-chloropropylamine hydrochloride which was collected by filtration, and the filter cake washed twice with 1500 ml. portions of acetone. The washed crystals weighed about 500 g. and melted at 181°-3° C. with decomposition. An additional 30 g. of compound were obtained from the acetone wash by standard crystallization procedures. The structure of the above compound was verified by NMR and titration.

Workup

  1. additionA solution containing 442 g
  2. temperatureto maintain
  3. temperaturereflux
  4. temperatureThe solution was refluxed an additional 5 hours
  5. customEvaporation of the chloroform andd other volatile constituents in vacuo

Sources & evidence

ORD record
ord-10a60a479308452080acae8c313dcc6f
Source dataset
uspto-grants-1986_12
Patent number
US04626549

Reaction notes

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