HCID 9827709, compound → HCID 21925672, compound

HRID 1611909Notes

Reaction equation

HRID 1611909 reaction equation
[CH2:1]([N:8]([CH3:27])[C:9](=O)[CH2:10][N:11]1[C:24]2[CH:23]=[C:22]([Cl:25])[CH:21]=[CH:20][C:19]=2[S:18][C:17]2[C:12]1=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1COCC1.Cl.CO>[CH2:1]([N:8]([CH2:9][CH2:10][N:11]1[C:24]2[CH:23]=[C:22]([Cl:25])[CH:21]=[CH:20][C:19]=2[S:18][C:17]2[C:12]1=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH3:27])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 1

HCID 9827709HCID 9827709, compound

Product 1

HCID 21925672HCID 21925672, compoundYield 118.3%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

N-Benzyl-2-(2-chlorophenothiazin-10-yl)-N-methylacetamide (140 mg, 0.355 mmol) was dissolved in THF (5 mL). A solution of borane• THF complex in THF (1.0 M, 5 mL, 5 mmol) was added, and the solution heated to reflux for 4 h. The mixture was carefully diluted with saturated HCl in methanol and stirred for 30 min. The solvent was removed under vacuum, and the residue dissolved in ethyl acetate and aqueous sodium hydroxide (1 N). The layers were separated and the aqueous layer extracted with ethyl acetate. The organic layers were combined, dried (Na2SO4), filtered, and concentrated to provide benzyl-[2-(2-chlorophenothiazin-10-yl)-ethyl]methyl amine as a white solid (160 mg). The crude product was purified by SiO2 chromatography to provide pure product (50 mg, 34%) and 100 mg of impure product. The pure product was dissolved in acetone and a solution of fumaric acid (0.8 mL, 0.02 g/mL in methanol) was added. The solvents were removed under vacuum, and the residue slurried in chloroform and filtered to provide the sub-titled compound (47 mg) as an off-white solid.

Workup

  1. temperaturethe solution heated
  2. temperatureto reflux for 4 h
  3. customThe solvent was removed under vacuum
  4. dissolutionthe residue dissolved in ethyl acetate
  5. customThe layers were separated
  6. extractionthe aqueous layer extracted with ethyl acetate
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-ca3d64d34faa47c4b3bf763574e6928f
Source dataset
uspto-grants-2006_01
Patent number
US06992082B2

Reaction notes

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