N-Methylbenzylamine → HCID 9827709, compound

HRID 1611908Notes

Reaction equation

HRID 1611908 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[S:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]([CH2:16][C:17]([OH:19])=O)[C:4]=2[CH:3]=1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[CH3:42][NH:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1.[OH-].[Na+]>C1COCC1.O.C(Cl)Cl>[CH2:44]([N:43]([CH3:42])[C:17](=[O:19])[CH2:16][N:5]1[C:4]2[CH:3]=[C:2]([Cl:1])[CH:15]=[CH:14][C:13]=2[S:12][C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1

Participants

9

Reactant 5

HCID 7669N-Methylbenzylamine2×HCID 14798Sodium HydroxideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21925664HCID 21925664, compound

Product 1

HCID 9827709HCID 9827709, compoundYield 40%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

(2-Chlorophenothiazin-10-yl)acetic acid (480 mg, 1.65 mmol) was dissolved in THF (10 mL). To this solution, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.58 g, 8.25 mmol), 1-hydroxybenzotriazole (220 mg, 1.65 mmol), and N-methyl benzyl amine (2.0 mL, 16.5 mmol) were added. The mixture was stirred at room temperature overnight and was then diluted with water and methylene chloride. The aqueous layer was made basic with sodium hydroxide (1N), and the layers were separated. The aqueous layer was extracted with methylene chloride. The organic layers were combined, washed with water and brine, dried (Na2SO4), filtered, and concentrated to provide a mixture of N-methyl benzyl amine and product (3.8 g). The residue was purified with a plug of SiO2. The product was recrystallized from hexane and ethyl acetate to provide N-benzyl-2-(2-chlorophenothiazin-10-yl)-N-methylacetamide as a white solid (258 mg, 40%).

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted with methylene chloride
  3. washwashed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto provide
  8. customThe residue was purified with a plug of SiO2
  9. customThe product was recrystallized from hexane and ethyl acetate

Sources & evidence

ORD record
ord-ff957d63a3024052a79dc3c63a27eb11
Source dataset
uspto-grants-2006_01
Patent number
US06992082B2

Reaction notes

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