p-Toluenesulfonic acid → HCID 22293645, compound

HRID 967402Notes

Reaction equation

HRID 967402 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=2[CH2:22][CH:23](OC)OC)[CH2:10][CH2:9]1)=O)(C)(C)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:21][C:19]1[CH:20]=[C:15]2[C:16]([CH:22]=[CH:23][N:14]2[CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 69156905HCID 69156905, compound

Product 1

HCID 22293645HCID 22293645, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 1.03 g (2.59 mmol) of 4-[5-chloro-2-(2,2-dimethoxy-ethyl)-phenylamino]-piperidine-1-carboxylic acid tert-butyl ester in 15 mL toluene was added 1.0 g (5.2 mmol) of p-toluenesulfonic acid. The reaction mixture was heated to 60° C. for 20 min, allowed to cool to room temperature and quenched with 100 mL of sat. aqueous NaHCO3 then extracted with EtOAc (3×75 mL). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated to afford 590 mg (98%) of the desired product as a pink oil. MS (electrospray): exact mass calculated for C13H15ClN2, 234.09. m/z found, 235.1 [M+H]+. 1H NMR (CDCl3, 400 MHz, a mixture of amide rotamers): 7.52 (d, J=8.34 Hz, 1H), 7.38 (br s, 1H), 7.21 (d, J=3.28 Hz, 1H), 7.06 (dd, J=8.34, 1.77 Hz, 1H), 6.49 (d, J=3.28 Hz, 1H), 4.24 (m, 1H), 3.30 (m, 2H), 2.85 (dt, J=12.38, 2.53 Hz, 2H), 2.08 (m, 2H), 1.94 (m, 2H).

Workup

  1. temperatureto cool to room temperature
  2. customquenched with 100 mL of sat. aqueous NaHCO3
  3. extractionthen extracted with EtOAc (3×75 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e94691efbe3043468a3c5d462b4c6a8c
Source dataset
uspto-grants-2005_10
Patent number
US06953793B2

Reaction notes

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