Chloroform → 3,4-Dichloro-N-(1-methyl-1-azaspiro[4.5]decan-4-yl)benzamide

HRID 1388178Notes

Reaction equation

HRID 1388178 reaction equation
C(O)(=O)/C=C/C(O)=O.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.C([O-])(O)=O.[Na+].Cl[C:35]1[CH:43]=[C:42]([Cl:44])[CH:41]=[CH:40][C:36]=1[C:37](Cl)=[O:38].C(Cl)(Cl)[Cl:46]>>[CH3:17][N:18]1[C:22]2([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]2)[CH:21]([NH:28][C:37](=[O:38])[C:36]2[CH:40]=[CH:41][C:42]([Cl:44])=[C:43]([Cl:46])[CH:35]=2)[CH2:20][CH2:19]1

Participants

5

Reactant 4

HCID 6212Chloroform2×HCID 666452,4-Dichlorobenzoyl chlorideHCID 516892Sodium BicarbonateHCID 70447095HCID 70447095, compound

Product 1

HCID 132828563,4-Dichloro-N-(1-methyl-1-azaspiro[4.5]decan-4-yl)benzamide

Procedure

To a stirring suspension of 3.0 g (0.017 mole) of 1-methyl-4-amino-azaspiro[4.5]decane of Example 2 and 5.0 g of NaHCO3 in 50 ml of CHCl3 was added dropwise 3.8 g (0.018 mole) of 2,4-dichlorobenzoyl chloride in 25 ml of CHCl3. The reaction was refluxed for 3 hours, cooled to room temperature, filtered, and the solvent evaporated to give an oil. The residue was triturated with boiling hexane and decanted; the hexane solution afforded 3.1 g of 1-methyl-4-(3,4-dichlorobenzamido)-1-azaspiro[4.5]decane on standing. The solid was dissolved in ether and a solution of ethereal HCl was added. The resulting solid was collected and recrystallized three times from ethanol to give 2.4 g (37.5%) m.p. 227°-229° C. of 1-methyl-4-(2,4-dichlorobenzamido)-1-azaspiro[4.5]decane hydrochloride.

Workup

  1. temperatureThe reaction was refluxed for 3 hours
  2. filtrationfiltered
  3. customthe solvent evaporated
  4. customto give an oil
  5. customThe residue was triturated with boiling hexane
  6. customdecanted

Sources & evidence

ORD record
ord-18089f04acb44fc3b40404971a876de2
Source dataset
uspto-grants-1984_02
Patent number
US04430335

Reaction notes

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