Sodium Hydroxide → HCID 21413781, compound

HRID 2071415Notes

Reaction equation

HRID 2071415 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][C:10]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[C:17]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH:16]=2)(O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>Cl.C(Cl)Cl>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]=[C:10]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[C:17]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH:16]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 13599048HCID 13599048, compound

Product 1

HCID 21413781HCID 21413781, compoundYield 52.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1.5 g of the product of Step A in 15 ml of 2N hydrochloric acid was refluxed for 6 hours and after cooling, the mixture was diluted with methylene chloride. The mixture was made alkaline with sodium hydroxide addition and the methylene chloride phase was recovered by decanting, was dried and evaporated to dryness. The residue was chromatographed over silica gel and elution with a 90-5-5 cyclohexane-chloroform-triethylamine mixture yielded 0.76 g of N-benzyl-3-(3',4'-dibenzyloxyphenyl)-1,2,5,6-tetrahydropyridine.

Workup

  1. temperaturewas refluxed for 6 hours
  2. temperatureafter cooling
  3. customthe methylene chloride phase was recovered
  4. customby decanting
  5. customwas dried
  6. customevaporated to dryness
  7. customThe residue was chromatographed over silica gel and elution with a 90-5-5 cyclohexane-chloroform-triethylamine mixture

Sources & evidence

ORD record
ord-fee3620ed9284d768a941a76ba507bd4
Source dataset
uspto-grants-1977_09
Patent number
US04046901

Reaction notes

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