Triethylamine → HCID 20569916, compound

HRID 1894475Notes

Reaction equation

HRID 1894475 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH3:15])[CH2:10][CH2:9]1)=O)(C)(C)C.C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>ClCCl>[CH3:15][N:14]([CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1)[S:24]([CH3:23])(=[O:26])=[O:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 15380702tert-Butyl 4-(methylamino)piperidine-1-carboxylate

Product 1

HCID 20569916HCID 20569916, compoundYield 150.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-methylamino-piperidine-1-carboxylic acid tert-butyl ester (1.20 g, 5.58 mmole, Astatech) and triethylamine (3.2 mL, 22.95 mmole) in dichloromethane (70 mL) at 0° C. was added methanesulfonyl chloride (724 mg, 6.287 mmole, Aldrich). The mixture was allowed to stir for 30 min before washed successively with aqueous sodium bicarbonate and water and concentrated to dryness. The residue was taken up in dichloromethane (20 mL), treated with trifluoroacetic acid (20 mL) and allowed to stir for 3 h before it was concentrated to dryness. The residue was dissolved in dichloromethane, washes with aqueous sodium bicarbonate and concentrated to give N-methyl-N-piperidin-4-yl-methanesulfonamide (1.61 g) which was used without further purification.

Workup

  1. washbefore washed successively with aqueous sodium bicarbonate and water
  2. concentrationconcentrated to dryness
  3. additiontreated with trifluoroacetic acid (20 mL)
  4. stirringto stir for 3 h before it
  5. concentrationwas concentrated to dryness
  6. dissolutionThe residue was dissolved in dichloromethane
  7. concentrationwith aqueous sodium bicarbonate and concentrated

Sources & evidence

ORD record
ord-85ee707c67b54fd6ac7b71d460f363cb
Source dataset
uspto-grants-2013_08
Patent number
US08513239B2

Reaction notes

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