Methanol → Methyl 4-(3-amino-3-methylbutyl)benzoate

HRID 1065251Notes

Reaction equation

HRID 1065251 reaction equation
S(Cl)(Cl)=O.Cl.[C:6]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([CH3:20])([CH3:19])[NH2:18])=[CH:11][CH:10]=1)([OH:8])=[O:7].[CH3:21]O>>[C:6]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([CH3:20])([CH3:19])[NH2:18])=[CH:11][CH:10]=1)([O:8][CH3:21])=[O:7]

Participants

4

Reactant 3

HCID 887Methanol2×HCID 24386Thionyl ChlorideHCID 705332913-(4-Carboxyphenyl)-1, 1-dimethylpropanamine hydrochloride

Product 1

HCID 20501354Methyl 4-(3-amino-3-methylbutyl)benzoate

Procedure

Thionyl chloride (31 ml) was added dropwise to methanol (210 ml) at -70°. The solution was stirred for 10 mins and then 3-(4-carboxyphenyl)-1, 1-dimethylpropanamine hydrochloride (20 g) in methanol was added dropwise. The reaction mixture was allowed to warm to ambient temperature and then heated under reflux for 1 h. The solvent was evaporated, the residue partitioned between potassium carbonate and ether and the organic layer dried. Removal of the solvent gave the title compound, as an oil.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1 h
  3. customThe solvent was evaporated
  4. customthe residue partitioned between potassium carbonate and ether
  5. customthe organic layer dried
  6. customRemoval of the solvent

Sources & evidence

ORD record
ord-aa614a6c80914366886fbea556a5d1a9
Source dataset
uspto-grants-1982_05
Patent number
US04329358

Reaction notes

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