Hydrochloric Acid → HCID 86590496, compound

HRID 1453981Notes

Reaction equation

HRID 1453981 reaction equation
[C:1]([C@H:5]1[C@@H:11]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH2:10][C@H:9]2[N:19]([CH3:20])[C@@H:6]1[CH2:7][CH2:8]2)(=O)[CH2:2][CH3:3].C[NH:22][OH:23].Cl.[C:25](=O)(O)[O-].[K+]>CO>[CH3:25][O:23][N:22]=[C:1]([CH:5]1[CH:11]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH2:10][CH:9]2[N:19]([CH3:20])[CH:6]1[CH2:7][CH2:8]2)[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 11647MethylhydroxylamineHCID 516893Potassium BicarbonateHCID 10446100HCID 10446100, compound

Product 1

HCID 86590496HCID 86590496, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The ketone, 2β-(1-Propanoyl)-3β-(4-fluorophenyl)tropane, is dissolved in an appropriate organic solvent such as methanol and then at room temperature the desired alkyl-hydroxyl-amine, such as methyl-hydroxyl-amine, is added in excess (1.01 to 10 equivalents but preferably 5 equivalents). This amine is added as its hydrochloride or as a free base. If a salt is used such as a hydrochloride then an equivalent amount of mild base should be added, such as potassium bicarbonate or other equivalent salt in order to neutralize the amine hydrochloride. If necessary the solution is boiled until reaction occurs, typically 15 minutes to 24 hours is needed. The desired oxime, 1-[3-(4-Fluoro-phenyl)-8-methyl-8-aza-bicyclo[3.2.1]oct-2-yl]-propan-1-one O-methyl-oxime is isolated as an E, Z-mixture and if so desired separated by flash silica gel chromatography to provide either the pure E or pure Z-compound. The pH of the reaction solution is most preferably about 4 but may range from 1-12. See, for example, Morgan et al. J. Am. Chem. Soc. 1994, 116(8),3251-3260.

Workup

  1. customIf necessary the solution is boiled until reaction
  2. waitoccurs, typically 15 minutes to 24 hours

Sources & evidence

ORD record
ord-45229c9b85794134854c9cddc59f9351
Source dataset
uspto-grants-2009_01
Patent number
US07476740B2

Reaction notes

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