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

HRID 1446927Notes

Reaction equation

HRID 1446927 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 and 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 and other volatile constituents in vacuo

Sources & evidence

ORD record
ord-1a41500d2fa745afa4fa65d2e44a408b
Source dataset
uspto-grants-1982_02
Patent number
US04314081

Reaction notes

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