Carbon Dioxide → 2-(4-Chlorobenzyl)-1-methylperhydroazepine

HRID 27424Notes

Reaction equation

HRID 27424 reaction equation
C(OC([C:6](=[C:14]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][N:15]1[CH3:21])[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1)=O)C.C(=O)=O.[OH-].[Na+]>Cl>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([CH2:6][CH:14]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][N:15]2[CH3:21])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 14798Sodium HydroxideHCID 539415482-(alpha-Ethoxycarbonyl-4-chlorobenzylidene)-1-methylperhydroazepine

Product 1

HCID 233428522-(4-Chlorobenzyl)-1-methylperhydroazepineYield 36.7%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Boil 15.5 g of 2-(α-ethoxycarbonyl-4-chlorobenzylidene)- 1-methylperhydroazepine and 110 ml of concentrated hydrochloric acid under reflux until the evolution of CO2 ceases. Cool the resulting reaction mixture to ambient temperature; then alkalize it with caustic soda solution (while cooling with ice) and extract the product with diethyl ether. Concentrate the ether phase and dry the prepared concentrate over sodium sulfate. Dissolve the residual 2-(4-chlorobenzylidene)-1-methylperhydroazepine (7.44 g) in ethyl alcohol and hydrogenate with platinum/active carbon/hydrogen. Filter the catalyst from the hydrogenated product, distil off the solvent and then distil the remainder under a high vacuum to obtain 4.4 g of the title compound with a BP of 102° to 110° at 0.003 mm of Hg.

Workup

  1. temperatureCool
  2. customthe resulting reaction mixture to ambient temperature
  3. extractionextract the product with diethyl ether
  4. concentrationConcentrate the ether phase
  5. customdry the prepared
  6. concentrationconcentrate over sodium sulfate
  7. dissolutionDissolve the residual 2-(4-chlorobenzylidene)-1-methylperhydroazepine (7.44 g) in ethyl alcohol
  8. filtrationFilter the catalyst from the hydrogenated product
  9. customdistil off the solvent
  10. customdistil the remainder under a high vacuum

Sources & evidence

ORD record
ord-9cb96ea3457a47809df237889174aaf9
Source dataset
uspto-grants-1980_09
Patent number
US04221788

Reaction notes

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