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

HRID 883401Notes

Reaction equation

HRID 883401 reaction equation
[C:1]1([N:7]2[C:11]([CH2:12][CH2:13][CH3:14])=[CH:10][C:9]([CH2:15][CH2:16][CH:17]=O)=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:19][CH:20]1[CH2:25][NH:24][CH2:23][CH2:22][N:21]1[C:26]1[CH:27]=[C:28]([CH3:32])[CH:29]=[CH:30][CH:31]=1.CCN(C(C)C)C(C)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[CH3:19][CH:20]1[CH2:25][N:24]([CH2:17][CH2:16][CH2:15][C:9]2[CH:10]=[C:11]([CH2:12][CH2:13][CH3:14])[N:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[N:8]=2)[CH2:23][CH2:22][N:21]1[C:26]1[CH:27]=[C:28]([CH3:32])[CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 4

HCID 81531DiisopropylethylamineHCID 27238042-Methyl-1-(m-tolyl)piperazineHCID 5049666Sodium triacetoxyborohydrideHCID 866399313-(1-phenyl-5-propyl-1H-pyrazol-3-yl)propanal

Product 1

HCID 685552062-methyl-4-(3-(1-phenyl-5-propyl-1H-pyrazol-3-yl)propyl)-1-m-tolylpiperazine

Procedure

68 mg (45%) of target compound was obtained by using a method same as in Example 1 by using 3-(1-phenyl-5-propyl-1H-pyrazol-3-yl)propanal (80 mg, 0.330 mmol), 2-methyl-1-m-tolylpiperazine (63 mg, 0.330 mmol), DIPEA (0.090 mL, 0.495 mmol) and NaBH(OAc)3 (210 mg, 0.990 mmol).

Workup

  1. custom68 mg (45%) of target compound was obtained

Sources & evidence

ORD record
ord-daa7dde1ea29426684d4a98ae1c2e02a
Source dataset
uspto-grants-2012_08
Patent number
US08236806B2

Reaction notes

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