Acetic Acid → HCID 9830391, compound

HRID 2229804Notes

Reaction equation

HRID 2229804 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([CH:6]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[C:21](O)(=O)[CH3:22].[CH:25](=O)[CH2:26][CH:27]=O.[C:30]([BH3-])#[N:31].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]([N:13]2[CH2:14][CH2:15][N:16]([CH2:25][CH2:26][CH2:27][N:13]3[CH2:6][CH2:7][N:31]([CH:30]([C:21]4[CH:22]=[CH:8][CH:9]=[CH:10][CH:11]=4)[C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[CH:20][CH:19]=4)[CH2:15][CH2:14]3)[CH2:17][CH2:18]2)[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 9340NorchlorcyclizineHCID 10964MalonaldehydeHCID 5003444Sodium cyanoborohydride

Product 1

HCID 9830391HCID 9830391, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-(4-chlorobenzhydryl)piperazine 1 (obt. from Aldrich; 2 mmols) in methanol (8 mL) is acidified with acetic acid to pH 6.5 (pH meter) under a nitrogen atmosphere. Malonaldehyde (1 mmol) is added neat followed by sodium cyanoborohydride (3.1 mmols). The progress of the reaction is followed by thin layer chromatography. After the reaction is complete, the reaction solution is quenched in water and the pH of the aqueous mixture is adjusted to greater than 10 with aqueous NaOH. The mixture is extracted with ether, the organic extracts are washed with half-saturated saline, dried (Na2SO4), filtered and concentrated under reduced pressure to give the crude product. The desired compound 1,3-bis-[4-(4-chlorobenzhydryl)piperazin-1-yl]propane 2 (R=—CH2—; R1=Cl; R2=H) is obtained by purification of the crude product with the use of HPLC.

Workup

  1. customthe reaction solution is quenched in water
  2. extractionThe mixture is extracted with ether
  3. washthe organic extracts are washed with half-saturated saline
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give the crude product

Sources & evidence

ORD record
ord-def05c55434d458789a221048290577f
Source dataset
uspto-grants-2002_07
Patent number
US06420560B1

Reaction notes

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