Acetaldehyde → HCID 21060157, compound

HRID 885882Notes

Reaction equation

HRID 885882 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13](=[O:15])[CH3:14])=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH3:16][CH:17]=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH2:16]([N:4]1[CH2:5][CH2:6][N:1]([C:7]2[CH:8]=[CH:9][C:10]([C:13](=[O:15])[CH3:14])=[CH:11][CH:12]=2)[CH2:2][CH2:3]1)[CH3:17]

Participants

5

Reactant 3

HCID 177AcetaldehydeHCID 97269Piperazin-4-ylacetophenoneHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 21060157HCID 21060157, compoundYield 43.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(4-piperazin-1-yl-phenyl)-ethanone (500 mg, 2.45 mmol), CH3CHO (161 mg, 3.67 mmol) and NaBH(OAc)3 (778 mg, 3.67 mmol) in DCM (15 ml) was stirred at room temperature overnight. The resulting solution was partitioned between water and DCM and the organic phase was extracted with 1 M HCl. The aqueous layer was brought to basic conditions with NH4OH, extracted with AcOEt and then the organic phase was dried over Na2SO4 and evaporated in vacuo to give 250 mg of 1-[4-(4-ethyl-piperazin-1-yl)-phenyl]-ethanone.

Workup

  1. customThe resulting solution was partitioned between water and DCM
  2. extractionthe organic phase was extracted with 1 M HCl
  3. extractionextracted with AcOEt
  4. dry with materialthe organic phase was dried over Na2SO4
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-ac494812942e44a0b855630e8c778342
Source dataset
uspto-grants-2012_08
Patent number
US08242175B2

Reaction notes

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