L-Tartaric acid → HCID 68574649, compound

HRID 2111911Notes

Reaction equation

HRID 2111911 reaction equation
[CH3:1][CH:2]([CH3:19])[CH2:3][N:4]([CH2:11][C:12]1[S:16][C:15]([CH3:17])=[N:14][C:13]=1[CH3:18])[CH:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]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].[CH3:1][CH:2]([CH3:19])[CH2:3][N:4]([CH2:11][C:12]1[S:16][C:15]([CH3:17])=[N:14][C:13]=1[CH3:18])[CH:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 444305L-Tartaric acidHCID 57640316HCID 57640316, compound

Product 1

HCID 68574649HCID 68574649, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-(2-Methylpropyl)-N-[(2,4-dimethyl-1,3-thiazol-5-yl)methyl]piperidin-4-amine (0.70 g, 2.49 mmol) and L-tartaric acid (0.37 g, 2.49 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 (1.05 g, 98%) N-(2-methylpropyl)-N-[(2,4-dimethyl-1,3-thiazol-5-yl)methyl]piperidin-4-amine tartrate: mass spectrum (ion spray): m/z=282.2 (M+1); 1H NMR (CD3OD): δ=4.45 (2H, s), 3.77 (2H, s), 3.47 (2H, brd), 3.00-2.91 (2H, m), 2.88-2.79 (1H, m), 2.62 (3H, s), 2.34-2.30 (5H, m), 1.99 (2H, brd), 1.85-1.70 (3H, m), 0.93 (6H, d).

Workup

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

Sources & evidence

ORD record
ord-877a274bc9e54ccfbe8a2e7e0466e3e8
Source dataset
uspto-grants-2009_04
Patent number
US07521462B2

Reaction notes

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