Hydrochloric Acid → N-Methyl-N-(2-pyrrolidinylmethyl)methanesulfonamide

HRID 2403411Notes

Reaction equation

HRID 2403411 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:13][N:14]([S:16]([CH3:19])(=[O:18])=[O:17])[CH3:15])=O)(C)(C)C.Cl>ClCCl.C(OCC)C>[CH3:15][N:14]([CH2:13][CH:9]1[CH2:10][CH2:11][CH2:12][NH:8]1)[S:16]([CH3:19])(=[O:18])=[O:17]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 666177341,1-Dimethylethyl 2-[[methyl(methylsulfonyl)amino]methyl]-1-pyrrolidinecarboxylate

Product 1

HCID 66617803N-Methyl-N-(2-pyrrolidinylmethyl)methanesulfonamideYield 118.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[(methanesulfonyl-methyl-amino)-methyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (0.63 g) in dichloromethane (10 mL) at room temperature was added hydrogen chloride (3.0 mL of a 2 M solution in diethyl ether). The reaction mixture was stirred at room temperature for 72 h and then reduced in vacuo to give N-methyl-N-pyrrolidin-2-ylmethyl-methanesulfonamide as a crystalline solid (0.49 g).

Sources & evidence

ORD record
ord-809e19cccb9447c9acf0f00e6029a4af
Source dataset
uspto-grants-2014_08
Patent number
US08802670B2

Reaction notes

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