Sodium Hydroxide → HCID 67222831, compound

HRID 521017Notes

Reaction equation

HRID 521017 reaction equation
N([O-])=O.[Na+].Cl.Cl.[NH:7]1[CH2:12][CH2:11][CH2:10][C@@H:9]2[C:13]3[CH:14]=[CH:15][C:16](N)=[CH:17][C:18]=3[CH2:19][C@H:8]12.[OH-:21].[Na+]>O.S(=O)(=O)(O)O>[NH:7]1[CH2:12][CH2:11][CH2:10][C@@H:9]2[C:13]3[CH:14]=[CH:15][C:16]([OH:21])=[CH:17][C:18]=3[CH2:19][C@H:8]12

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 23668193Sodium NitriteHCID 67223225HCID 67223225, compound

Product 1

HCID 67222831HCID 67222831, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
120 °C

Procedure

Sodium nitrite (92 mg) dissolved in water (0.5 mL) is added dropwise to a solution of cis-2,3,4,4a,9,9a-hexahydro-1H-indeno[2,1-b]pyridin-7-ylamine dihydrochloride (0.30 g) in half-concentrated sulfuric acid (0.6 ml) chilled in an ice bath. The solution is stirred for 15 min in the cooling bath prior to the addition of half-concentrated sulfuric acid (5 ml). The resulting solution is heated to 120° C. and stirred at this temperature for 3 h. The mixture is cooled to room temperature, diluted with water, and basified with 4 M NaOH. The resulting mixture is extracted with ethyl acetate and the combined extracts are dried (Na2SO4). The solvent is evaporated and the residue is chromatographed on silica gel [dichloromethane/(dichloromethane/methanol/NH4OH 50:48:2) 80:20→40:60] to give the title compound. Yield: 0.07 g (32% of theory); LC (method 1): tR=0.83 min; Mass spectrum (ESI+): m/z=190 [M+H]+.

Workup

  1. temperaturechilled in an ice bath
  2. stirringstirred at this temperature for 3 h
  3. temperatureThe mixture is cooled to room temperature
  4. extractionThe resulting mixture is extracted with ethyl acetate
  5. dry with materialthe combined extracts are dried (Na2SO4)
  6. customThe solvent is evaporated
  7. customthe residue is chromatographed on silica gel [dichloromethane/(dichloromethane/methanol/NH4OH 50:48:2) 80:20→40:60]

Sources & evidence

ORD record
ord-9d9eea2c1df244f39ee08b9ef788faa6
Source dataset
uspto-grants-2016_05
Patent number
US09328072B2

Reaction notes

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