Benzoyl chloride → HCID 20471604, compound

HRID 1388179Notes

Reaction equation

HRID 1388179 reaction equation
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].C(O)(=O)/C=C/C(O)=O.[CH3:17][N:18]1[C:22]2([CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[CH:21]([NH2:28])[CH2:20][CH2:19]1.[OH-].[Na+].[C:31](Cl)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C(O)(=O)/C=C/C(O)=O>C(#N)C>[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].[CH3:17][N:18]1[C:22]2([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]2)[CH:21]([NH:28][C:31](=[O:38])[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:20][CH2:19]1

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 14798Sodium HydroxideHCID 444972Fumaric AcidHCID 70447095HCID 70447095, compound

Product 1

HCID 20471604HCID 20471604, compoundYield 25.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirring suspension of 3.5 g (0.021 mole) of 1-methyl-4-amino-1-azaspiro[4.5]decane of Example 2 and 150 ml of 10% NaOH was added dropwise 3.1 g (0.022 mole) of benzoyl chloride. The reaction was stirred vigorously for 24 hours, the aqueous solution was decanted and the remaining oil was dissolved in ethyl acetate and dried over Na2SO4. The solvent was then evaporated to give a solid which was recrystallized from hexane to give 2.5 g. The solid was dissolved in 10 ml of acetonitrile and 1.1 g of fumaric acid was added. The suspension was stirred until the amine salt precipitated from solution. The compound was filtered and recrystallized twice from ethanol-ether to give 2.1 g (25.7%) of 1-methyl-4-benzamido-1-azaspiro[4.5]decane fumarate, m.p. 171°-173° C.

Workup

  1. customthe aqueous solution was decanted
  2. dissolutionthe remaining oil was dissolved in ethyl acetate
  3. dry with materialdried over Na2SO4
  4. customThe solvent was then evaporated
  5. customto give a solid which
  6. customwas recrystallized from hexane
  7. customto give 2.5 g
  8. customprecipitated from solution
  9. filtrationThe compound was filtered
  10. customrecrystallized twice from ethanol-ether

Sources & evidence

ORD record
ord-b0a073c75c0747f59a7f4445a8b3cf33
Source dataset
uspto-grants-1984_02
Patent number
US04430335

Reaction notes

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