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

HRID 386994Notes

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[CH:22]=[C:23]([N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[CH:24]=[CH:25][C:26]=1[CH3:27].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:23]3[CH:24]=[CH:25][C:26]([CH3:27])=[C:21]([CH3:20])[CH:22]=3)[CH2:29][CH2:30]2)=[N:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 4

HCID 81531Diisopropylethylamine

HCID 27237821-(3,4-Xylyl)piperazine

HCID 5049666Sodium triacetoxyborohydride

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

Product 1

HCID 250646451-(3-(1-tert-butyl-5-phenyl-1H-pyrazol-3-yl)propyl)-4-(3,4-dimethylphenyl)piperazine

Procedure

62 mg (71%) 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-(3,4-dimethylphenyl)piperazine (35.4 mg, 0.186 mmol), DIPEA (49 mL, 0.279 mmol) and NaBH(OAc)3 (118 mg, 0.558 mmol).

Workup

custom62 mg (71%) of target compound was obtained

Sources & evidence

ORD record: ord-50577d882f4d4afcb83ed3d4145d7d8f
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372844B2

Reaction notes

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