Potassium Iodide → HCID 67264526, compound

HRID 1687553Notes

Reaction equation

HRID 1687553 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[CH:11]=[CH:10][C:9]2[CH:12]=[CH:13][C:14]([O:16][CH3:17])=[CH:15][C:8]=2[CH2:7][C:6]1=[O:18].Cl.[CH3:20][NH:21][CH3:22].[I-].[K+].C(=O)([O-])[O-].[K+].[K+].C([O-])([O-])=O.[Na+].[Na+]>C(#N)C>[CH3:20][N:21]([CH3:22])[CH2:2][CH2:3][CH2:4][N:5]1[CH:11]=[CH:10][C:9]2[CH:12]=[CH:13][C:14]([O:16][CH3:17])=[CH:15][C:8]=2[CH2:7][C:6]1=[O:18]

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 10473Dimethylamine, hydrochlorideHCID 11430Potassium CarbonateHCID 204337693-(3-Chloro-propyl)-8-methoxy-1,3-dihydro-benzo[d]azepin-2-one

Product 1

HCID 67264526HCID 67264526, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Into a 1-neck round-bottom flask was added 3-(3-chloro-propyl)-8-methoxy-1,3-dihydro-benzo[d]azepin-2-one (2.5 g, 0.0094 mol), dimethylamine hydrochloride (1.534 g, 0.01882 mol), Potassium iodide (0.468 g, 0.00282 mol), and Potassium carbonate (5.201 g, 0.03763 mol), in Acetonitrile (25 mL), and the reaction was stirred over night at 50° C. The reaction mixture was next partitioned between water and dichloromethane, and the layers were separated. The aqueous phase was extracted once with dichloromethane and the combined organic extract was washed with water. The organic solution was next extracted twice with 100 mL HCl solution (˜4N), and the aqueous extract was washed once with dichloromethane (50 mL). The aqueous solution of the chlorohydrate thus obtained was basified with solid Na2CO3 to pH 11. Extraction with dichloromethane, drying of the extracts (MgSO4), concentration and high vacuum drying provided 3-(3-dimethylamino-propyl)-8-methoxy-1,3-dihydro-benzo[d]azepin-2-one, which was used without further purification (oil, 1.13 g, 44%). LC/MS (ESI+) 275 (M+1).

Workup

  1. customThe reaction mixture was next partitioned between water and dichloromethane
  2. customthe layers were separated
  3. extractionThe aqueous phase was extracted once with dichloromethane
  4. extractionthe combined organic extract
  5. washwas washed with water
  6. extractionnext extracted twice with 100 mL HCl solution (˜4N)
  7. extractionthe aqueous extract
  8. washwas washed once with dichloromethane (50 mL)
  9. customThe aqueous solution of the chlorohydrate thus obtained
  10. extractionExtraction with dichloromethane
  11. dry with materialdrying of the extracts (MgSO4), concentration and high vacuum
  12. customdrying

Sources & evidence

ORD record
ord-43f933959e6a458bae1049b9315c0343
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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