Acetic Acid → HCID 18694313, compound

HRID 1870868Notes

Reaction equation

HRID 1870868 reaction equation
[CH3:1][N:2]1[CH:7]2[CH2:8][CH2:9][CH:3]1[CH2:4][C:5]([C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1)(O)[CH2:6]2.C(O)(=O)C.Cl.[C:23]([OH:30])(=[O:29])/[CH:24]=[CH:25]/[C:26]([OH:28])=[O:27]>C(OCC)C.CO>[C:23]([OH:30])(=[O:29])/[CH:24]=[CH:25]/[C:26]([OH:28])=[O:27].[CH3:1][N:2]1[CH:7]2[CH2:8][CH2:9][CH:3]1[CH:4]=[C:5]([C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1)[CH2:6]2

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 434533HCID 434533, compoundHCID 444972Fumaric Acid

Product 1

HCID 18694313HCID 18694313, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

The title compound was prepared from 8-methyl-3-(4-methylphenyl)-8-azabicyclo[3.2.1]octan-3-ol (3.4 g, 14.7 mmol), glacial acetic acid (11 mL) and concentrated hydrochloric acid (11 mL). The free base of the title compound was dissolved in diethyl ether and added fumaric acid (1.3 g, 11.2 mmol) in methanol. The resulting solution was concentrated to dryness, the residue was trituated in diethyl ether, the title compound precipitated as powder and was isolated by filtration. Yield 2.46 g (51%) m.p. 156.8-157.4° C.

Workup

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

Sources & evidence

ORD record
ord-f7df5b9b129b43b3b7b30f16aba072ea
Source dataset
uspto-grants-2000_08
Patent number
US06100275

Reaction notes

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