Hydrochloric Acid → HCID 23282476, compound

HRID 369969Notes

Reaction equation

HRID 369969 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]2[CH2:8][CH2:9][CH2:10][NH:11][CH2:12][C:6]=2[CH:5]=1)([O-:3])=[O:2].[OH-].[Na+].[CH2:17]1[O:19][CH2:18]1.[ClH:20]>C(O)C.CCOCC>[ClH:20].[OH:19][CH2:18][CH2:17][N:11]1[CH2:10][CH2:9][CH2:8][C:7]2[CH:13]=[CH:14][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]=2[CH2:12]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6354Ethylene OxideHCID 14798Sodium HydroxideHCID 103753148-Nitro-2,3,4,5-tetrahydro-1H-benzo[c]azepine

Product 1

HCID 23282476HCID 23282476, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent3×HCID 3283Diethyl EtherSolvent

Procedure

To a suspension of 8-nitro-2,3,4,5-tetrahydro-1H-2-benzazapine (5.08 g, 22.2 mmol) in ethanol (200 ml) at 0° C. was added 2.5M sodium hydroxide solution (10.0 ml). To this solution, in a pressure bottle, was added ethylene oxide (4.2 ml) and the bottle was capped and stirred at ambient temperature overnight. The solvent was concentrated in vacuo and the residue was partitioned between dichloromethane and dilute sodium hydroxide. The organic phase was dried (magnesium sulfate) and concentrated to give a yellow solid. This solid was taken up in ethanol and acidified with hydrochloric acid in ethanol. Addition of ether effected precipitation of the title salt as an orange solid (2.69 g, 44%). m.p. 193.5-4.5° C.

Workup

  1. customthe bottle was capped
  2. concentrationThe solvent was concentrated in vacuo
  3. customthe residue was partitioned between dichloromethane and dilute sodium hydroxide
  4. dry with materialThe organic phase was dried (magnesium sulfate)
  5. concentrationconcentrated
  6. customto give a yellow solid
  7. customprecipitation of the title salt as an orange solid (2.69 g, 44%)

Sources & evidence

ORD record
ord-2b64db0425d446e38ed383ca3d71be99
Source dataset
uspto-grants-2000_10
Patent number
US06140322

Reaction notes

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