Triethylamine → tert-butyl 4-(N-methylmethanesulfonamido)piperidine-1-carboxylate

HRID 881420Notes

Reaction equation

HRID 881420 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH3:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]([S:24]([CH3:23])(=[O:26])=[O:25])[CH3:15])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

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

Product 1

HCID 60540093tert-butyl 4-(N-methylmethanesulfonamido)piperidine-1-carboxylateYield 79.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-methylamino-piperidine-1-carboxylic acid tert-butyl ester (1.72 g, 8 mmol) in dichloromethane (10 mL) was added triethylamine (1.30 mL, 8.8 mmol) followed by methanesulphonyl chloride (0.68 mL, 8.8 mmol). After stirring for 16 hours the reaction mixture was then diluted with dichloromethane, washed with sodium bicarbonate solution, dried (MgSO4) and the solvent removed in vacuo. The residue was purified by flash chromatography using 50% ethyl acetate in petroleum ether as the eluent to yield 4-(methanesulfonyl-methyl-amino)-piperidine-1-carboxylic acid tert-butyl ester as a white solid (1.85 g, 75%). Treatment of this compound with trifluoroacetic acid in dichloromethane yielded N-methyl-N-piperidin-4-yl-methanesulfonamide, which was isolated as the TFA salt.

Workup

  1. washwashed with sodium bicarbonate solution
  2. dry with materialdried (MgSO4)
  3. customthe solvent removed in vacuo
  4. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-446f5721486c465c90d428e0c762cfde
Source dataset
uspto-grants-2015_03
Patent number
US08993563B2

Reaction notes

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