Acetic Acid → (+/-)3-(4-Chlorophenyl)-8-methyl-8-azabicyclo[3.2.1]oct-2-ene Malonate

HRID 1870866

Reaction equation

HRID 1870866 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2(O)[CH2:14][CH:13]3[N:15]([CH3:16])[CH:10]([CH2:11][CH2:12]3)[CH2:9]2)=[CH:4][CH:3]=1.C(O)(=O)C.Cl.[C:23]([OH:29])(=[O:28])[CH2:24][C:25]([OH:27])=[O:26]>C(O)C>[C:23]([OH:29])(=[O:28])[CH2:24][C:25]([OH:27])=[O:26].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH2:9][CH:10]3[N:15]([CH3:16])[CH:13]([CH2:12][CH2:11]3)[CH:14]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 4344883-(4-Chlorophenyl)-8-methyl-8-azabicyclo[3.2.1]octan-3-ol

Product 1

HCID 18694314(+/-)3-(4-Chlorophenyl)-8-methyl-8-azabicyclo[3.2.1]oct-2-ene Malonate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

The title compound was prepared from 3-(4-chlorophenyl)-8-methyl-8-azabicyclo[3.2.1]octan-3-ol (4 g, 16 mmol), glacial acetic acid (15 mL) and concentrated hydrochloric acid (15 mL). Yield of free base (3.6 g, 97%). Some of the free base (1.44 g, 6 mmol) was dissolved in ethanol (96%) and added malonic acid (0.62 g, 6 mmol) in ethanol (96%). The resulting solution was concentrated to an oil, the oil was trituated in diethyl ether, the title compound precipitated as powder and was isolated by filtration. Yield (1.4 g, 71%) as white crystals m.p. 100.8-102.1° C.

Workup

  1. concentrationThe resulting solution was concentrated to an oil
  2. customthe title compound precipitated as powder
  3. customwas isolated by filtration

Sources & evidence

ORD record
ord-2fbe958019e241fa8796086258e6865d
Source dataset
uspto-grants-2000_08
Patent number
US06100275

Linked notes

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