Fumaric Acid → N-(2-Methylpropyl)-N-[(quinolin-3-yl)methyl]piperidin-4-amine fumarate

HRID 2111892Notes

Reaction equation

HRID 2111892 reaction equation
[CH3:1][CH:2]([CH3:22])[CH2:3][N:4]([CH2:11][C:12]1[CH:13]=[N:14][C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1.[C:23]([OH:30])(=[O:29])/[CH:24]=[CH:25]/[C:26]([OH:28])=[O:27]>C(OCC)C.CO>[C:23]([OH:30])(=[O:29])/[CH:24]=[CH:25]/[C:26]([OH:28])=[O:27].[CH3:1][CH:2]([CH3:22])[CH2:3][N:4]([CH2:11][C:12]1[CH:13]=[N:14][C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:5]1[CH2:6][CH2:7][NH:8][CH2:9][CH2:10]1

Participants

5

Reactant 2

HCID 444972Fumaric AcidHCID 57640314N-(2-methylpropyl)-N-[(quinolin-3-yl)methyl]piperidin-4-amine

Product 1

HCID 68574554N-(2-Methylpropyl)-N-[(quinolin-3-yl)methyl]piperidin-4-amine fumarateYield 76.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 3283Diethyl EtherSolvent2×

Procedure

N-(2-Methylpropyl)-N-[(quinolin-3-yl)methyl]piperidin-4-amine (0.74 g, 2.50 mmol) is dissolved in diethyl ether (35 ml) and methanol (6 ml). Fumaric acid (0.29 g, 2.50 mmol), in warm methanol (4 ml), is then added. Diethyl ether (100 ml) is added and the solution is heated. The solution is slowly cooled and then placed in the freezer. The solid is filtered and washed with diethyl ether to yield (0.79 g, 76%) of the title product: mass spectrum (ion spray): m/z=298.1 (M+1); 1H NMR (DMSO-d6): δ=8.84 (d, 1H), 8.16 (d, 1H), 7.98-7.91 (m, 2H), 7.71-7.68 (m, 1H), 7.58-7.54 (m, 1H), 6.42 (s, 2H), 3.75 (s, 2H), 3.25-3.22 (m, 2H), 2.76-2.70 (m, 3H), 2.21 (d, 2H), 1.83-1.59 (m, 6H), 0.76 (d, 6H).

Workup

  1. temperaturethe solution is heated
  2. temperatureThe solution is slowly cooled
  3. filtrationThe solid is filtered
  4. washwashed with diethyl ether

Sources & evidence

ORD record
ord-aecd0983cc464ee784cff57d8d0a4ce1
Source dataset
uspto-grants-2009_04
Patent number
US07521462B2

Reaction notes

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