Diethylamine → HCID 178463830, compound

HRID 1626248Notes

Reaction equation

HRID 1626248 reaction equation
[I-:1].[Cl:2][C:3]1[C:16]2[C:7](=[S+:8][C:9]3[C:14]([N:15]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:6]=[CH:5][CH:4]=1.[CH2:17]([NH:19][CH2:20][CH3:21])[CH3:18].[C:22]([N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23]>C(Cl)(Cl)Cl.CO>[I-:1].[C:25]([O:24][C:22]([N:29]1[CH2:30][CH2:31][N:32]([C:11]2[CH:10]=[C:9]3[C:14](=[CH:13][CH:12]=2)[N:15]=[C:16]2[C:7]([CH:6]=[C:5]([N:19]([CH2:20][CH3:21])[CH2:17][CH3:18])[CH:4]=[C:3]2[Cl:2])=[S+:8]3)[CH2:33][CH2:34]1)=[O:23])([CH3:28])([CH3:27])[CH3:26]

Participants

6

Reactant 3

HCID 8021DiethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 86666998HCID 86666998, compound

Product 1

HCID 178463830HCID 178463830, compoundYield 1.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

1-Chlorophenothiazin-5-ium Iodide (350 mg, 0.473 mmol) was dissolved in CHCl3 (5 mL) and diethylamine (0.1 mL, 1.04 mmol) was added. The resulting mixture was allowed to stir at RT for 24 h. The solvent was removed and the crude material was used without purification. The crude material was dissolved in MeOH (5 mL) and 1-Boc-piperazine (177 mg, 0.95 mmol) was added as a solution in MeOH (2 mL) and thje mixture was stirred for 24 h. The solvent was evaporated and a portion of the material was purified by prep TLC to give 5.2 mg of a product.

Workup

  1. customThe solvent was removed
  2. customthe crude material was used without purification
  3. dissolutionThe crude material was dissolved in MeOH (5 mL)
  4. stirringthje mixture was stirred for 24 h
  5. customThe solvent was evaporated
  6. customa portion of the material was purified by prep TLC

Sources & evidence

ORD record
ord-59bad829de2240b4aedbfc8269c6e592
Source dataset
uspto-grants-2014_07
Patent number
US08785434B2

Reaction notes

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