Hydrochloric Acid → 85181-38-0

HRID 1381285Notes

Reaction equation

HRID 1381285 reaction equation
[CH3:1][N:2]1[C@@H:6]2[CH2:7][CH:8]([OH:10])[CH2:9][C@H:3]1[CH2:4][CH2:5]2.Cl.[CH3:12][C:13]1[CH:14]=[C:15]([CH:19]=[C:20]([CH3:22])[CH:21]=1)[C:16]([Cl:18])=[O:17].Cl.C(=O)([O-])[O-].[K+].[K+]>O>[CH3:22][C:20]1[CH:19]=[C:15]([C:16]([O:10][CH:8]2[CH2:9][C@H:3]3[N:2]([CH3:1])[C@H:6]([CH2:5][CH2:4]3)[CH2:7]2)=[O:17])[CH:14]=[C:13]([CH3:12])[CH:21]=1.[ClH:18]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid3×HCID 11430Potassium CarbonateHCID 810883,5-Dimethylbenzoyl ChlorideHCID 2005992292-08-2

Product 1

HCID 6859985181-38-0Yield 58.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred mixture of tropine hydrochloride (5.27 g) and 3,5-dimethylbenzoyl chloride (5 g) is heated at 130°-140° C. for 30 minutes during which time the mixture liquifies, evolves hydrogen chloride gas and resolidifies. A solution of the cooled solid in water is basified with a solution of potassium carbonate and the base extracted with ethyl acetate. The ethyl acetate solution is washed several times with water, dried over magnesium sulphate, and evaporated to yield the free base which is converted to the hydrochloride by the addition of ethereal hydrogen chloride. Recrystallization of the precipitated solid from ethanol yields tropyl 3,5-dimethylbenzoate hydrochloride (5.4 g) m.p. 260° C.

Workup

  1. temperatureis heated at 130°-140° C. for 30 minutes during which time the mixture
  2. extractionthe base extracted with ethyl acetate
  3. washThe ethyl acetate solution is washed several times with water
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customto yield the free base which
  7. customRecrystallization of the precipitated solid from ethanol

Sources & evidence

ORD record
ord-1ec1d0d72edb4c37b52d021ebed60454
Source dataset
uspto-grants-1986_04
Patent number
US04585866

Reaction notes

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