4-(3-Methoxyphenyl)piperidine-1-propanamine → 4-[3-[[[[3-[4-(3-Methoxyphenyl)-1-piperidinyl]propyl]-amino]carbonothioyl]amino]phenyl]-1,4-dihydro-2,6-dimethyl-3,5-pyrazinedicarboxylic acid, dimethyl ester

HRID 566906Notes

Reaction equation

HRID 566906 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:25])=[C:5]([C:21]([O:23][CH3:24])=[O:22])[N:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N:18]=[C:19]=[S:20])[CH:13]=2)[C:7]=1[C:8]([O:10][CH3:11])=[O:9].[CH3:26][O:27][C:28]1[CH:29]=[C:30]([CH:34]2[CH2:39][CH2:38][N:37]([CH2:40][CH2:41][CH2:42][NH2:43])[CH2:36][CH2:35]2)[CH:31]=[CH:32][CH:33]=1>C1C=CC=CC=1>[CH3:26][O:27][C:28]1[CH:29]=[C:30]([CH:34]2[CH2:39][CH2:38][N:37]([CH2:40][CH2:41][CH2:42][NH:43][C:19]([NH:18][C:14]3[CH:13]=[C:12]([N:6]4[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:2]([CH3:1])[NH:3][C:4]([CH3:25])=[C:5]4[C:21]([O:23][CH3:24])=[O:22])[CH:17]=[CH:16][CH:15]=3)=[S:20])[CH2:36][CH2:35]2)[CH:31]=[CH:32][CH:33]=1

Participants

4

Reactant 2

HCID 120432914-(3-Methoxyphenyl)piperidine-1-propanamineHCID 155242381,4-Dihydro-2,6-dimethyl-4-(3-isothiocyanatophenyl)-3,5-pyrazinedicarboxylic acid, dimethyl ester

Product 1

HCID 98302974-[3-[[[[3-[4-(3-Methoxyphenyl)-1-piperidinyl]propyl]-amino]carbonothioyl]amino]phenyl]-1,4-dihydro-2,6-dimethyl-3,5-pyrazinedicarboxylic acid, dimethyl esterYield 95%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

1,4-Dihydro-2,6-dimethyl-4-(3-isothiocyanatophenyl)-3,5-pyrazinedicarboxylic acid, dimethyl ester (500 mg, 1.4 mmol) was refluxed with 4-(3-methoxyphenyl)-piperidine-1-propanamine (380 mg, 1.5 mmol) in 8 mL of benzene for 2 hours. Chromatographic purification (on silica gel, 100% methylene chloride first, followed by 10% (v/v) methanol in methylene chloride) of the residue after concentration in vacuo gave the title compound as a yellow foam (807 mg, 95%); 1H-NMR (CDCl3) δ 7.61 (br, 1H), 7.20 (t, 1H, J=7.9 Hz), 7.12 (t, 1H, J=8.1 Hz), 6.88 (br, 1H), 6.60 (m, 3H), 6.57 (dd, 1H, J=8.3, 2.1 Hz), 6.47 (br, 1H), 3.78 (s, 3H), 3.73 (s, 6H), 3.60-3.80 (m, 2H), 2.94 (m, 2H), 2.37 (s, 6H), 2.25-2.50 (m, 3H), 2.03 (m, 2H), 1.60-1.85 (m, 4H), 1.40-1.60 (m, 2H); 13C-NMR (CDCl3) δ 166.0, 159.6, 152.5, 149.2, 147.7, 130.2, 129.5, 119.5, 115.8, 113.1, 112.2, 111.1, 109.7, 108.8, 63.6, 55.2, 54.2, 51.8, 42.5, 32.8, 25.4, and 18.0.

Workup

  1. customChromatographic purification (on silica gel, 100% methylene chloride first
  2. concentrationafter concentration in vacuo

Sources & evidence

ORD record
ord-7ee8f0d78f1b4f0fa0ea0eccdeee0d46
Source dataset
uspto-grants-2001_01
Patent number
US06177429B1

Reaction notes

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