Acetic Acid → HCID 9830391、化合物

反応式

[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

参加物

実験手順

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.