Diisopropylethylamine → 1-(3-(1-tert-butyl-5-p-tolyl-1H-pyrazol-3-yl)propyl)-4-(4-methoxyphenyl)piperazine

HRID 883301Notes

Reaction equation

[C:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)=[CH:8][C:7]([CH2:17][CH2:18][CH:19]=O)=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)=[CH:25][CH:24]=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:11]=[CH:12][C:13]([CH3:16])=[CH:14][CH:15]=2)=[CH:8][C:7]([CH2:17][CH2:18][CH2:19][N:32]2[CH2:33][CH2:34][N:29]([C:26]3[CH:25]=[CH:24][C:23]([O:22][CH3:21])=[CH:28][CH:27]=3)[CH2:30][CH2:31]2)=[N:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 4

HCID 81531Diisopropylethylamine

HCID 2697221-(4-Methoxyphenyl)piperazine

HCID 5049666Sodium triacetoxyborohydride

HCID 866399173-(1-tert-butyl-5-p-tolyl-1H-pyrazol-3-yl)propanal

Product 1

HCID 250654571-(3-(1-tert-butyl-5-p-tolyl-1H-pyrazol-3-yl)propyl)-4-(4-methoxyphenyl)piperazine

Procedure

77 mg (72%) of target compound was obtained by using a method same as in Example 1 by using 3-(1-tert-butyl-5-p-tolyl-1H-pyrazol-3-yl)propanal (60 mg, 0.222 mmol), 1-(4-methoxyphenyl)piperazine (43 mg, 0.222 mmol), DIPEA (0.06 mL, 0.333 mmol) and NaBH(OAc)3 (141 mg, 0.666 mmol).

Workup

custom77 mg (72%) of target compound was obtained

Sources & evidence

ORD record: ord-34b61a02a73c4de3ae74bae05f803bd1
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08236806B2

Reaction notes

Loading…