p-Anisoyl chloride → HCID 131713379, compound

HRID 1388180Notes

Reaction equation

HRID 1388180 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:40])[C:32]1[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[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:40])[C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=2)[CH2:20][CH2:19]1.[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:40])[C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=2)[CH2:20][CH2:19]1

Participants

6

Reactant 4

HCID 7477p-Anisoyl chlorideHCID 14798Sodium HydroxideHCID 444972Fumaric AcidHCID 70447095HCID 70447095, compound

Product 1

HCID 131713379HCID 131713379, compoundYield 15.9%

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 3.8 g (0.022 mole) of p-anisoyl chloride. The reaction was stirred vigorously for 5 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 4.4 g. The solid was dissolved in 20 ml of acetonitrile and 1.7 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 1.2 g (15.8%) of 1-methyl-4-(4-methoxybenzamido)-1-azaspiro[4.5]decane hemifumarate, m.p. (softens at 110° C.) 152°-155° 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 4.4 g
  8. customprecipitated from solution
  9. filtrationThe compound was filtered
  10. customrecrystallized twice from ethanol-ether

Sources & evidence

ORD record
ord-b92155aae44f43dfaaa3f236a5c93a41
Source dataset
uspto-grants-1984_02
Patent number
US04430335

Reaction notes

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