Bis(2-Methoxyethyl)amine → HCID 178495926, compound

HRID 1626246Notes

Reaction equation

HRID 1626246 reaction equation
[I-:1].[CH:2]1[C:15]2[C:6](=[S+:7][C:8]3[C:13]([N:14]=2)=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:5]=[CH:4][CH:3]=1.[CH3:16][O:17][CH2:18][CH2:19][NH:20][CH2:21][CH2:22][O:23][CH3:24].[C:25]([N:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1)([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26]>C(Cl)(Cl)Cl.CO>[I-:1].[CH3:16][O:17][CH2:18][CH2:19][N:20]([CH2:21][CH2:22][O:23][CH3:24])[C:4]1[CH:3]=[CH:2][C:15]2[C:6]([CH:5]=1)=[S+:7][C:8]1[C:13](=[CH:12][CH:11]=[C:10]([N:35]3[CH2:34][CH2:33][N:32]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:37][CH2:36]3)[CH:9]=1)[N:14]=2

Participants

6

Reactant 3

HCID 2383Bis(2-Methoxyethyl)amineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 86666993HCID 86666993, compound

Product 1

HCID 178495926HCID 178495926, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

Phenothiazin-5-ium iodide (400 mg, 0.567 mmol) was dissolved in CHCl3 (20 mL) and bis(2-methoxyethyl)amine (0.17 mL, 1.13 mmol) was added dropwise. The mixture was stirred at RT overnight. The solvent was removed and the material was used without purification. The salt (200 mg, 0.281 mol) was dissolved in MeOH (20 mL) and a solution of N-Boc piperazine (105 mg, 0.562 mmol) was added. The mixture was stirred for 24 hrs and the solvent was removed by evaporation. The crude material was purified by flash silica gel chromatography to give a dark blue solid of the desired product.

Workup

  1. customThe solvent was removed
  2. customthe material was used without purification
  3. stirringThe mixture was stirred for 24 hrs
  4. customthe solvent was removed by evaporation
  5. customThe crude material was purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-5e0213fe3afa49208c337d63a12462e5
Source dataset
uspto-grants-2014_07
Patent number
US08785434B2

Reaction notes

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