Mandelic Acid → HCID 13929038, compound

HRID 1251366Notes

Reaction equation

HRID 1251366 reaction equation
[C:1]([OH:11])(=[O:10])[CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3].[CH3:12][CH:13]1[CH2:18][CH2:17][CH2:16][NH:15][CH2:14]1>C(OCC)(=O)C>[C:1]([OH:11])(=[O:10])[CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3].[CH3:12][C@H:13]1[CH2:18][CH2:17][CH2:16][NH:15][CH2:14]1

Participants

4

Reactant 2

HCID 1292Mandelic AcidHCID 790813-Methylpiperidine

Product 1

HCID 13929038HCID 13929038, compoundYield 30.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(+) mandelic acid (45.64 g, 0.3 mol) is dissolved in 300 ml of warm ethyl acetate. 3-methylpiperidine (29.8 g, 0.3 mol) is added under agitation and the solution allowed to return to ambient temperature. After 24 hours, the salt obtained is filtered and rinsed with an EA/AcOEt (1/1) mixture then recrystallized 3 times from AcOEt. In this way, the (S)-(+)-3-methylpiperidine mandelate salt (22.7 g) is obtained. M.p.=120-122° C; αD=+58.0° (methanol, c=1.0).

Workup

  1. customto return to ambient temperature
  2. customthe salt obtained
  3. filtrationis filtered
  4. washrinsed with an EA/AcOEt (1/1) mixture
  5. customthen recrystallized 3 times from AcOEt

Sources & evidence

ORD record
ord-47395a219b794e2e8a6e8c534a55d801
Source dataset
uspto-grants-2002_01
Patent number
US06342511B1

Reaction notes

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