1-(2,4-Xylyl)piperazine → 1-(2,4-dimethylphenyl)-4-(3-(1-phenyl-5-p-tolyl-1H-pyrazol-3-yl)propyl)piperazine

HRID 387023

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][C:24]1[CH:29]=[C:28]([CH3:30])[CH:27]=[CH:26][C:25]=1[N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1.CCN(C(C)C)C(C)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[CH3:23][C:24]1[CH:29]=[C:28]([CH3:30])[CH:27]=[CH:26][C:25]=1[N:31]1[CH2:32][CH2:33][N:34]([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)[CH2:35][CH2:36]1

Participants

Reactant 4

HCID 705441-(2,4-Xylyl)piperazine

HCID 81531Diisopropylethylamine

HCID 5049666Sodium triacetoxyborohydride

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

Product 1

HCID 250656591-(2,4-dimethylphenyl)-4-(3-(1-phenyl-5-p-tolyl-1H-pyrazol-3-yl)propyl)piperazine

Procedure

113 mg (82%) 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), 1-(2,4-dimethylphenyl)piperazine (53 mg, 0.276 mmol), DIPEA (0.072 mL, 0.414 mmol) and NaBH(OAc)3 (175 mg, 0.828 mmol).

Workup

custom113 mg (82%) of target compound was obtained

Sources & evidence

ORD record: ord-012071c9e55340adad600d5b3e1f8b4d
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372844B2

Linked notes

Loading…