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

HRID 1073563Notes

Reaction equation

HRID 1073563 reaction equation
[CH3:1][N:2]([CH3:13])[CH2:3][CH2:4][CH:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)O.[ClH:14].S(Cl)([Cl:17])=O>C(Cl)Cl>[ClH:17].[Cl:14][CH:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:4][CH2:3][N:2]([CH3:13])[CH3:1]

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 6344DichloromethaneSolvent

Procedure

(+-)3-dimethylamino-l-phenyl-1-propanol (10) (19 g) was dissolved in CH2Cl2 (200 ml). The solution was saturated with HCl (g). Thionyl chloride (17 ml) was added dropwise over 20 min. resulting in slight reflux. Subsequental reflux for 5 h resulted in the formation of a precipitate. Cooling and evaporation of the reaction mixture resulted in a yellowish crystalline mass, which was rinsed by several washings with acetone, resulting in colourless crystals of the title compound identified by 1H NMR.

Workup

  1. customresulting in slight reflux
  2. temperatureSubsequental reflux for 5 h
  3. customresulted in the formation of a precipitate
  4. temperatureCooling
  5. customevaporation of the reaction mixture
  6. customresulted in a yellowish crystalline mass, which
  7. washwas rinsed by several washings with acetone

Sources & evidence

ORD record
ord-1198828da7d242f9a3dd507584179e9a
Source dataset
uspto-grants-1990_11
Patent number
US04970232

Reaction notes

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