Hydrochloric Acid → HCID 69115392, compound

HRID 2054168Notes

Reaction equation

HRID 2054168 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])=[CH:4][C:3]=1[CH:19]1[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]1.Cl>C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])=[CH:4][C:3]=1[CH:19]1[CH2:20][CH2:21][NH:22][CH2:23][CH2:24]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69115646HCID 69115646, compound

Product 1

HCID 69115392HCID 69115392, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-{2-methyl-5-[(phenylmethoxy)carbonylamino]phenyl}piperidine carboxylate (7.50 g, 17.6 mmol) was dissolved in CH2Cl2 (120 mL) and a HCl solution (4M in dioxane, 52.0 mL) was added and stirred for 1 h. The mixture was concentrated in vacuo and redissolved in CH2Cl2. Aqueous Na2CO3 solution (1 M) was added and the biphasic mixture was stirred for 20 min and separated. The organic layer was further washed with water, dried over Na2SO4 and concentrated in vacuo to afford N-(4-methyl-3-(4-piperidyl)phenyl)(phenylmethoxy)carboxamide (5.61 g, 98% yield) as a white solid. ESMS m/e: 326.0 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionredissolved in CH2Cl2
  3. additionAqueous Na2CO3 solution (1 M) was added
  4. stirringthe biphasic mixture was stirred for 20 min
  5. customseparated
  6. washThe organic layer was further washed with water
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-091e5278c786411d871a9fd5573ffdcc
Source dataset
uspto-grants-2008_02
Patent number
US07329656B2

Reaction notes

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