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

HRID 1381038Notes

Reaction equation

HRID 1381038 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 added to the chloroform solution at a rate sufficient to maintain reflux. Reflux was continued for an additional 5 hours. Evaporation of the chloroform and other volatile constituents from the reaction mixture in vacuo yielded N,N-dimethyl 3-phenyl-3-chloropropylamine hydrochloride which was collected by filtration. The filter cake was washed twice with 1500 ml. portions of acetone. The washed crystals weighed about 500 g., and melted at 181°-183° 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. temperatureReflux
  5. customEvaporation of the chloroform and other volatile constituents from the reaction mixture in vacuo

Sources & evidence

ORD record
ord-20e5c8a7a4b84450ac67d56835079cd7
Source dataset
uspto-grants-1986_04
Patent number
US04584404

Reaction notes

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