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

HRID 883311Notes

Reaction equation

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

Participants

Reactant 4

HCID 81531Diisopropylethylamine

HCID 27238042-Methyl-1-(m-tolyl)piperazine

HCID 5049666Sodium triacetoxyborohydride

HCID 866399183-(1-phenyl-5-p-tolyl-1H-pyrazol-3-yl)propanal

Product 1

HCID 250658722-methyl-4-(3-(1-phenyl-5-p-tolyl-1H-pyrazol-3-yl)propyl)-1-m-tolylpiperazine

Procedure

112 mg (81%) of target compound was obtained by using a method same as in Example 1 by using 3-(1-phenyl-5-p-tolyl-1H-pyrazol-3-yl)propanal (80 mg, 0.276 mmol), 2-methyl-1-m-tolylpiperazine (53 mg, 0.276 mmol), DIPEA (0.072 mL, 0.414 mmol) and NaBH(OAc)3 (175 mg, 0.828 mmol).

Workup

custom112 mg (81%) of target compound was obtained

Sources & evidence

ORD record: ord-e6cacaeb09a943ea9baf5fbd214a15e7
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08236806B2

Reaction notes

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