Hydrochloric Acid → HCID 71280830, compound

HRID 406129Notes

Reaction equation

HRID 406129 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:34])[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([N:23]3[CH2:27][CH2:26][C@H:25]([N:28]4[CH2:32][CH2:31][CH2:30][C@@H:29]4[CH3:33])[CH2:24]3)=[CH:19][CH:18]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C1(S)C=CC=CC=1.[ClH:42]>O1CCOCC1>[ClH:42].[CH3:33][C@H:29]1[CH2:30][CH2:31][CH2:32][N:28]1[C@H:25]1[CH2:26][CH2:27][N:23]([C:20]2[CH:19]=[CH:18][C:17]([CH2:16][C:15]([NH:14][CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)=[O:34])=[CH:22][CH:21]=2)[CH2:24]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7969ThiophenolHCID 54597135HCID 54597135, compound

Product 1

HCID 71280830HCID 71280830, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

4-{2-[4-((2S,3′S)-2-Methyl-[1,3′]bipyrrolidinyl-1′-yl)-phenyl]-acetylamino}-piperidine-1-carboxylic acid tert-butyl ester (2.92 g, 6.2 mmol) was dissolved in 5 mL of dioxane. To this solution was added 1.0 g of PhSH, followed by addition of 4N HCl in dioxane (6.2 mL, 24.8 mmol, 4 equiv.). The solution was stirred at rt overnight. HCl was removed by passing N2 through the solution which was absorbed by NaOH aq solution. The solvent was removed by reduced pressure distillation. The residue was further dried under high vacuum to get 2.7 g (100%) of the title compound as a powder.

Workup

  1. customHCl was removed
  2. customwas absorbed by NaOH aq solution
  3. customThe solvent was removed by reduced pressure distillation
  4. customThe residue was further dried under high vacuum

Sources & evidence

ORD record
ord-67bbc4c5960f4bc996729423a9278254
Source dataset
uspto-grants-2014_06
Patent number
US08754095B2

Reaction notes

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