L-Tartaric acid → HCID 68576497, compound

HRID 2111920Notes

Reaction equation

HRID 2111920 reaction equation
[CH:1]1([CH2:4][N:5]([CH2:12][C:13]2[S:17][C:16]([CH3:18])=[N:15][C:14]=2[CH3:19])[CH:6]2[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)[CH2:3][CH2:2]1.[C:20]([OH:29])(=[O:28])[C@@H:21]([C@H:23]([C:25]([OH:27])=[O:26])[OH:24])[OH:22]>CO>[C:25]([CH:23]([CH:21]([C:20]([OH:29])=[O:28])[OH:22])[OH:24])([OH:27])=[O:26].[CH:1]1([CH2:4][N:5]([CH2:12][C:13]2[S:17][C:16]([CH3:18])=[N:15][C:14]=2[CH3:19])[CH:6]2[CH2:7][CH2:8][NH:9][CH2:10][CH2:11]2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 444305L-Tartaric acidHCID 57640328HCID 57640328, compound

Product 1

HCID 68576497HCID 68576497, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-(Cyclopropylmethyl)-N-[(2,4-dimethyl-1,3-thiazol-5-yl)methyl]piperidin-4-amine (1.25 g, 4.46 mmol) and L-Tartaric acid (0.67 g, 4.46 mmol) are dissolved in methanol (25 ml). The solution is stirred for 1.5 h and concentrated. The solid is dried in a vacuum oven overnight to yield (1.86 g, 97%) N-(cyclopropylmethyl)-N-[(2,4-dimethyl-1,3-thiazol-5-yl)methyl]piperidin-4-amine tartrate: mass spectrum (ion spray): m/z=280.2 (M+1); 1H NMR (CD3OD): δ=4.45 (2H, s), 3.87 (2H, s), 3.45 (2H, brs), 3.11-2.93 (3H, m), 2.62 (3H, s), 2.45 (2H, d), 2.32 (3H, s), 2.02 (2H, brd), 1.96-1.76 (2H, m), 0.95-0.85 (1H, m), 0.56-0.49 (2H, m), 0.17-0.10 (2H, m).

Workup

  1. concentrationconcentrated
  2. customThe solid is dried in a vacuum oven overnight

Sources & evidence

ORD record
ord-e754a1a911ab4e15ad98247761119a85
Source dataset
uspto-grants-2009_04
Patent number
US07521462B2

Reaction notes

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