Acetic Acid → 1-[1,1-Dimethylethoxycarbonyl]-4-[3-(1-methylpropyl)amino-2-pyridinyl]piperazine

HRID 864411Notes

Reaction equation

HRID 864411 reaction equation
[CH3:1][C:2]([CH3:20])([O:4][C:5]([N:7]1[CH2:12][CH2:11][N:10]([C:13]2[C:18]([NH2:19])=[CH:17][CH:16]=[CH:15][N:14]=2)[CH2:9][CH2:8]1)=[O:6])[CH3:3].[CH3:21][C:22](=O)[CH2:23][CH3:24].C(O)(=O)C>CO>[CH3:3][C:2]([CH3:20])([O:4][C:5]([N:7]1[CH2:8][CH2:9][N:10]([C:13]2[C:18]([NH:19][CH:22]([CH3:21])[CH2:23][CH3:24])=[CH:17][CH:16]=[CH:15][N:14]=2)[CH2:11][CH2:12]1)=[O:6])[CH3:1]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 6569Methyl Ethyl KetoneHCID 2756375tert-Butyl 4-(3-aminopyridin-2-yl)piperazine-1-carboxylate

Product 1

HCID 214776321-[1,1-Dimethylethoxycarbonyl]-4-[3-(1-methylpropyl)amino-2-pyridinyl]piperazine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Following the general procedure of PREPARATION 8 and making non-critical variations but starting with 1-[1,1-dimethylethoxycarbonyl]-4-[(3-amino)-2-pyridinyl)piperazine (International Publication No. WO 88/08424, 1.0 g), 2-butanone (0.27 g) sodium cyanoborohydride (0.23 g), acetic acid (5.1 ml) and methanol, the title compound is obtained, NMR (300 MHz, CDCl3) 7.68, 6.94, 6.86, 4.18, 3.56, 3.33, 3.05, 1.53, 1.47, 1.18 and 0.96 δ.

Workup

  1. customthe general procedure of PREPARATION 8

Sources & evidence

ORD record
ord-df18f0325b0d4494bbda7cf74517126a
Source dataset
uspto-grants-1996_10
Patent number
US05563142

Reaction notes

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