Formaldehyde → 1-[3-((3R,5S)-3,4,5-trimethyl-piperazin-1-yl)-phenyl]-ethanone

HRID 885854Notes

Reaction equation

HRID 885854 reaction equation
[CH3:1][C@H:2]1[NH:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[CH:10]=[C:11]([C:15](=[O:17])[CH3:16])[CH:12]=[CH:13][CH:14]=2)[CH2:3]1.[BH-](OC(C)=O)(OC(C)=O)O[C:20](C)=O.[Na+].C=O.[NH4+].[OH-]>C(Cl)Cl.O>[NH4+:4].[OH-:17].[CH3:8][C@H:6]1[N:7]([CH3:20])[C@@H:2]([CH3:1])[CH2:3][N:4]([C:9]2[CH:10]=[C:11]([C:15](=[O:17])[CH3:16])[CH:12]=[CH:13][CH:14]=2)[CH2:5]1

Participants

8

Reactant 4

HCID 712FormaldehydeHCID 14923Ammonium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 67049822cis-1-[3-(3,5-Dimethyl-piperazin-1-yl)-phenyl]-ethanone

Product 2

HCID 14923Ammonium HydroxideYield 3%HCID 582083601-[3-((3R,5S)-3,4,5-trimethyl-piperazin-1-yl)-phenyl]-ethanoneYield 156.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-[3-((3R,5S)-3,5-dimethyl-piperazin-1-yl)-phenyl]-ethanone (226 mg, 0.974 mmol), NaBH(OAc)3 (309 mg, 1.46 mmol) and CH2O (37% water solution, 0.087 ml, 1.17 mmol) in DCM (10 ml) was stirred at room temperature overnight. The resulting solution was diluted with water, brought to basic conditions with NH4OH and extracted with DCM. The organic phase was dried over Na2SO4 and evaporated in vacuo. The crude reaction mixture was purified by SCX cartridge (eluent: MeOH and then 3% NH4OH in MeOH) to give 188 mg of 1-[3-((3R,5S)-3,4,5-trimethyl-piperazin-1-yl)-phenyl]-ethanone.

Workup

  1. extractionextracted with DCM
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customevaporated in vacuo
  4. customThe crude reaction mixture
  5. customwas purified by SCX cartridge (eluent

Sources & evidence

ORD record
ord-c9557b043568477b80db5b3e20f9eded
Source dataset
uspto-grants-2012_08
Patent number
US08242175B2

Reaction notes

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