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

HRID 883391

Reaction equation

[C:1]([N:5]1[C:9]([CH2:10][CH2:11][CH:12]=O)=[CH:8][C:7]([CH2:14][CH2:15][CH3:16])=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[CH3:17][CH:18]1[CH2:23][NH:22][CH2:21][CH2:20][N:19]1[C:24]1[CH:25]=[C:26]([CH3:30])[CH:27]=[CH:28][CH: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]([CH2:10][CH2:11][CH2:12][N:22]2[CH2:21][CH2:20][N:19]([C:24]3[CH:25]=[C:26]([CH3:30])[CH:27]=[CH:28][CH:29]=3)[CH:18]([CH3:17])[CH2:23]2)=[CH:8][C:7]([CH2:14][CH2:15][CH3:16])=[N:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 4

HCID 81531Diisopropylethylamine

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

HCID 5049666Sodium triacetoxyborohydride

HCID 866399303-(1-tert-butyl-3-propyl-1H-pyrazol-5-yl)propanal

Product 1

HCID 685568044-(3-(1-tert-butyl-3-propyl-1H-pyrazol-5-yl)propyl)-2-methyl-1-m-tolylpiperazine

Procedure

190 mg (98%) of target compound was obtained by using a method same as in Example 1 by using 3-(1-tert-butyl-3-propyl-1H-pyrazol-5-yl)propanal (100 mg, 0.450 mmol), 2-methyl-1-m-tolylpiperazine (86 mg, 0.450 mmol), DIPEA (0.118 mL, 0.675 mmol) and NaBH(OAc)3 (286 mg, 1.350 mmol).

Workup

custom190 mg (98%) of target compound was obtained

Sources & evidence

ORD record: ord-e89d376282554754b21f30568435764e
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08236806B2

Linked notes

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