Diisopropylethylamine → 4-(3-(5-(4-chlorophenyl)-1-phenyl-1H-pyrazol-3-yl)propyl)-2-methyl-1-m-tolylpiperazine

HRID 883343Notes

Reaction equation

HRID 883343 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:11]=[C:10]([CH2:19][CH2:20][CH:21]=O)[CH:9]=2)=[CH:4][CH:3]=1.[CH3:23][CH:24]1[CH2:29][NH:28][CH2:27][CH2:26][N:25]1[C:30]1[CH:31]=[C:32]([CH3:36])[CH:33]=[CH:34][CH:35]=1.CCN(C(C)C)C(C)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:11]=[C:10]([CH2:19][CH2:20][CH2:21][N:28]3[CH2:27][CH2:26][N:25]([C:30]4[CH:31]=[C:32]([CH3:36])[CH:33]=[CH:34][CH:35]=4)[CH:24]([CH3:23])[CH2:29]3)[CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 81531DiisopropylethylamineHCID 27238042-Methyl-1-(m-tolyl)piperazineHCID 5049666Sodium triacetoxyborohydrideHCID 866399223-(5-(4-chlorophenyl)-1-phenyl-1H-pyrazol-3-yl)-propanal

Product 1

HCID 685595354-(3-(5-(4-chlorophenyl)-1-phenyl-1H-pyrazol-3-yl)propyl)-2-methyl-1-m-tolylpiperazine

Procedure

114 mg (85%) of target compound was obtained by using a method same as in Example 1 by using 3-(5-(4-chlorophenyl)-1-phenyl-1H-pyrazol-3-yl)-propanal (80 mg, 0.257 mmol), 2-methyl-1-m-tolylpiperazine (49 mg, 0.257 mmol), DIPEA (0.070 mL, 0.386 mmol) and NaBH(OAc)3 (163 mg, 0.771 mmol).

Workup

  1. custom114 mg (85%) of target compound was obtained

Sources & evidence

ORD record
ord-a6dae70d96f94fa398ad210581f511ea
Source dataset
uspto-grants-2012_08
Patent number
US08236806B2

Reaction notes

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