Trifluoroacetic acid → rac-3-(2,3-Dihydroxy-propoxy)-5-methoxy-N-piperidin-4-yl-benzamide trifluoroacetate

HRID 502437Notes

Reaction equation

HRID 502437 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:33])[C:16]2[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[C:18]([O:24][CH2:25][CH:26]3[CH2:30][O:29]C(C)(C)[O:27]3)[CH:17]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[F:34][C:35]([F:40])([F:39])[C:36]([OH:38])=[O:37]>C(Cl)Cl>[F:34][C:35]([F:40])([F:39])[C:36]([OH:38])=[O:37].[OH:27][CH:26]([CH2:30][OH:29])[CH2:25][O:24][C:18]1[CH:17]=[C:16]([CH:21]=[C:20]([O:22][CH3:23])[CH:19]=1)[C:15]([NH:14][CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1)=[O:33]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68456964Rac-4-[3-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-5-methoxy-benzoylamino]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 68458548rac-3-(2,3-Dihydroxy-propoxy)-5-methoxy-N-piperidin-4-yl-benzamide trifluoroacetateYield 136.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.45 g (3.1 mmol) of rac-4-[3-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-5-methoxy-benzoylamino]-piperidine-1-carboxylic acid tert-butyl ester was dissolved in 14 mL of MeCl2; while stirring, 2.39 mL (3.559 g=31.2 mmol) of trifluoroacetic acid was added drop by drop. After 16 hours, the reaction mixture was warmed up to reflux and stirred for another 21 hours; it was then evaporated and dried at high vacuum to yield 1.86 g of the crude title compound, which was used without further purification. MS: 325.4 (MH+).

Workup

  1. temperaturethe reaction mixture was warmed up
  2. temperatureto reflux
  3. stirringstirred for another 21 hours
  4. customit was then evaporated
  5. customdried at high vacuum

Sources & evidence

ORD record
ord-157f4dbc7915466ea258c55cb343737d
Source dataset
uspto-grants-2010_08
Patent number
US07772253B2

Reaction notes

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