L-Tartaric acid → [(4-chloro-thiazol-5-yl)methyl]-isobutyl-piperidin-4-yl-amine L-tartrate

HRID 2111934Notes

Reaction equation

HRID 2111934 reaction equation
[C:1]([OH:10])(=[O:9])[C@@H:2]([C@H:4]([C:6]([OH:8])=[O:7])[OH:5])[OH:3].[Cl:11][C:12]1[N:13]=[CH:14][S:15][C:16]=1[CH2:17][N:18]([CH2:25][CH:26]([CH3:28])[CH3:27])[CH:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1>C(O)C>[C:6]([C@@H:4]([C@H:2]([C:1]([OH:10])=[O:9])[OH:3])[OH:5])([OH:8])=[O:7].[Cl:11][C:12]1[N:13]=[CH:14][S:15][C:16]=1[CH2:17][N:18]([CH2:25][CH:26]([CH3:28])[CH3:27])[CH:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1

Participants

4

Reactant 2

HCID 444305L-Tartaric acid3×HCID 57640347[(4-Chloro-thiazol-5-yl)methyl]-isobutyl-piperidin-4-yl-amine

Product 1

HCID 68574467[(4-chloro-thiazol-5-yl)methyl]-isobutyl-piperidin-4-yl-amine L-tartrateYield 94.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Add L-tartaric acid (8.08 g, 53.8 mmol) to absolute ethanol (300 mL) and heat until the L-tartaric acid goes into solution. Add this warm solution of L-tartaric acid to [(4-chloro-thiazol-5-yl)methyl]-isobutyl-piperidin-4-yl-amine (15.50 g, 53.9 mmol) in absolute ethanol (200 mL) at room temperature. Stir for 18 hours under nitrogen at room temperature. Cool the reaction to 0° C. and filter off the solid. Wash the solid with cold absolute ethanol and dry in a vacuum oven at 50° C. to yield 22.16 g (94%) of [(4-chloro-thiazol-5-yl)methyl]-isobutyl-piperidin-4-yl-amine L-tartrate: mass spectrum (ion spray): m/z=288.1 (M+1); 1H NMR (CDCl3): δ=8.91 (s, 1H), 4.44 (s, 2H), 3.89 (s, 2H), 3.50-3.47 (m, 2H), 3.01-2.93 (m, 2H), 2.89-2.81 (m, 1H), 2.37 (d, 2H), 2.03-2.00 (m, 2H), 1.87-1.70 (m, 3H), 0.94 (d, 6H); 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 0.96 minutes, Purity: 100%.

Workup

  1. temperatureCool
  2. customthe reaction to 0° C.
  3. filtrationfilter off the solid
  4. washWash the solid with cold absolute ethanol
  5. customdry in a vacuum oven at 50° C.

Sources & evidence

ORD record
ord-304c85fb269643f8bc2c3bee4b2c5e64
Source dataset
uspto-grants-2009_04
Patent number
US07521462B2

Reaction notes

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