Hydrochloric Acid → HCID 9926899, compound

HRID 260914Notes

Reaction equation

HRID 260914 reaction equation
[N:1]12[CH2:8][CH2:7][CH2:6][C:5]1([CH2:9][N:10]([CH3:22])[C:11]1[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14](N)=[CH:13][CH:12]=1)[CH2:4][CH2:3][CH2:2]2.S(=O)(=O)(O)O.N([O-])=O.[Na+].[OH-].[Na+].[ClH:34]>O>[N:1]12[CH2:8][CH2:7][CH2:6][C:5]1([CH2:9][N:10]([C:11]1[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]([Cl:34])=[CH:13][CH:12]=1)[CH3:22])[CH2:4][CH2:3][CH2:2]2

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 10827724HCID 10827724, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 9926899HCID 9926899, compoundYield 14.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

To 6.31 g (21.4 mmol) of N-(1-azabicyclo[3.3.0]octan-5-yl)methyl-N-methyl-1,4-diaminonaphthalene, water (27.5 ml) and concentrated sulfuric acid (55 ml) were added to dissolve the compound therein. Sodium nitrite (1.40 g, 20.3 mmol) in water (8 ml) was added dropwise to the solution at a temperature of -5+ C. and then stirred for 15 minutes. Cuprous chloride (8.50 g, 85.9 mmol) suspended in concentric hydrochloric acid (18 ml) was added dropwise into the solution which was kept at 85° C. under stirring condition. After further stirring for 5 minutes, the reaction mixture was cooled by water with ice pieces. Several ice pieces were added to the reaction mixture which was made alkaline by adding 10% aqueous sodium hydroxide solution and extracted by chloroform. The resulting organic layer was dried over anhydrous sodium sulfate, concentrated in vacuo, purified by column chromatography to afford the desired compound (950 mg, 14.1% ), as a colorless liquid.

Workup

  1. dissolutionto dissolve the compound
  2. additionwas added dropwise into the solution which
  3. customwas kept at 85° C.
  4. stirringunder stirring condition
  5. stirringAfter further stirring for 5 minutes
  6. additionSeveral ice pieces were added to the reaction mixture which
  7. extractionextracted by chloroform
  8. dry with materialThe resulting organic layer was dried over anhydrous sodium sulfate
  9. concentrationconcentrated in vacuo
  10. custompurified by column chromatography

Sources & evidence

ORD record
ord-4dd7d8dc2df94dbdacd397a25be43ae8
Source dataset
uspto-grants-1996_06
Patent number
US05530138

Reaction notes

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