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

HRID 883281Notes

Reaction equation

[C:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:8][C:7]([CH2:16][CH2:17][CH:18]=O)=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[CH3:20][C:21]1[C:26]([CH3:27])=[CH:25][CH:24]=[CH:23][C:22]=1[N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1.CCN(C(C)C)C(C)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[C:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:8][C:7]([CH2:16][CH2:17][CH2:18][N:31]2[CH2:32][CH2:33][N:28]([C:22]3[CH:23]=[CH:24][CH:25]=[C:26]([CH3:27])[C:21]=3[CH3:20])[CH2:29][CH2:30]2)=[N:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 4

HCID 705411-(2,3-Xylyl)piperazine

HCID 81531Diisopropylethylamine

HCID 5049666Sodium triacetoxyborohydride

HCID 866399163-(1-tert-butyl-5-phenyl-1H-pyrazol-3-yl)propanal

Product 1

HCID 250646461-(3-(1-tert-butyl-5-phenyl-1H-pyrazol-3-yl)propyl)-4-(2,3-dimethylphenyl)piperazine

Procedure

39 mg (45%) of target compound was obtained by using a method same as in Example 1 by using 3-(1-tert-butyl-5-phenyl-1H-pyrazol-3-yl)propanal (50 mg, 0.195 mmol), 1-(2,3-dimethylphenyl)piperazine (35.4 mg, 0.186 mmol), DIPEA (49 mL, 0.279 mmol) and NaBH(OAc)3 (118 mg, 0.558 mmol).

Workup

custom39 mg (45%) of target compound was obtained

Sources & evidence

ORD record: ord-cdab1d7f0c794b8cac1ddda1bbb08a42
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08236806B2

Reaction notes

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