Methanol → HCID 86656722, compound

HRID 451545Notes

Reaction equation

HRID 451545 reaction equation
[NH2:1][C:2]1([CH3:15])[CH2:7][CH2:6][N:5](C(OC(C)(C)C)=O)[CH2:4][CH2:3]1.CO.O.[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25]([OH:28])(=[O:27])=[O:26])=[CH:21][CH:20]=1>CC(O)C>[CH3:29][C:19]1[CH:20]=[CH:21][C:22]([S:25]([OH:28])(=[O:27])=[O:26])=[CH:23][CH:24]=1.[CH3:29][C:19]1[CH:20]=[CH:21][C:22]([S:25]([OH:28])(=[O:27])=[O:26])=[CH:23][CH:24]=1.[CH3:15][C:2]1([NH2:1])[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 887MethanolHCID 521998p-Toluenesulfonic acid monohydrateHCID 11310432tert-Butyl 4-amino-4-methylpiperidine-1-carboxylate

Product 1

HCID 86656722HCID 86656722, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of tert-butyl 4-amino-4-methylpiperidine-1-carboxylate (1.96 g, 9.15 mmol) in MeOH (15.2 mmol) was added dropwise over 30 minutes to a solution of p-toluenesulfonic acid monohydrate (4.00 g, 21.0 mmol) in 2-propanol (7.9 mL) at 60° C. The reaction mixture was then heated to 60° C. for 16 h. After cooling to 0° C. the precipitate was filtered off and washed with 2-propanol and dried to give the title compound (3.91 g, 93%) as a white solid.

Workup

  1. temperatureAfter cooling to 0° C. the precipitate
  2. filtrationwas filtered off
  3. washwashed with 2-propanol
  4. customdried

Sources & evidence

ORD record
ord-f3dd9add6cf3426ca20ed7f054769278
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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