L-Tartaric acid → N-(2-Hydroxy-2-methylpropyl)-N-[(2,4-dichloro-1,3-thiazol-5-yl)methyl]piperidin-4-amine tartrate

HRID 2111938Notes

Reaction equation

HRID 2111938 reaction equation
[C:1]([OH:10])(=[O:9])[C@@H:2]([C@H:4]([C:6]([OH:8])=[O:7])[OH:5])[OH:3].[OH:11][C:12]([CH3:30])([CH3:29])[CH2:13][N:14]([CH2:21][C:22]1[S:26][C:25]([Cl:27])=[N:24][C:23]=1[Cl:28])[CH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1>CO>[C:6]([CH:4]([CH:2]([C:1]([OH:10])=[O:9])[OH:3])[OH:5])([OH:8])=[O:7].[OH:11][C:12]([CH3:30])([CH3:29])[CH2:13][N:14]([CH2:21][C:22]1[S:26][C:25]([Cl:27])=[N:24][C:23]=1[Cl:28])[CH:15]1[CH2:16][CH2:17][NH:18][CH2:19][CH2:20]1

Participants

4

Reactant 2

HCID 444305L-Tartaric acidHCID 57640324N-(2-hydroxy-2-methylpropyl)-N-[(2,4-dichloro-1,3-thiazol-5-yl)methyl]piperidin-4-amine

Product 1

HCID 68577145N-(2-Hydroxy-2-methylpropyl)-N-[(2,4-dichloro-1,3-thiazol-5-yl)methyl]piperidin-4-amine tartrateYield 97.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add L-tartaric acid (0.1504 g, 1.00 mmol) to a stirred solution of methanol (12 mL), and N-(2-hydroxy-2-methylpropyl)-N-[(2,4-dichloro-1,3-thiazol-5-yl)methyl]piperidin-4-amine (0.3386 g, 1.00 mmol). Stir the reaction for 2 hours at room temperature. Concentrate on a rotary evaporator to yield 0.4775 g (97%) of the title product: mass spectrum (ion spray): m/z=338.1 (M+1); LC/MS (90/5/5 to 0/95/5 water/acetonitrile/5% formic acid in water) XTerra MS C18 2.1 mm×50 mm×3.5 micron: Rt 1.64 minutes, Purity: >99%; 1H NMR (CD3OD): δ=4.44 (s, 2H), 4.04 (s, 2H), 3.49-3.46 (m, 2H), 2.99-2.86 (m, 3H), 2.55 (s, 2H), 2.05-2.02 (m, 2H), 1.80-1.71 (m, 2H), 1.24 (s, 6H).

Workup

  1. customthe reaction for 2 hours at room temperature
  2. concentrationConcentrate on a rotary evaporator

Sources & evidence

ORD record
ord-6c02f62b6dd84ea29033fd2758017458
Source dataset
uspto-grants-2009_04
Patent number
US07521462B2

Reaction notes

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