Triethylamine → 1-[(6-chloro-3-pyridinyl)sulfonyl]-N,N-dimethyl-4-Piperidinamine

HRID 79217

Reaction equation

HRID 79217 reaction equation
[CH3:1][N:2]([CH3:9])[CH:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.C(N(CC)CC)C.[Cl:17][C:18]1[N:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1.CO.C(Cl)Cl>CN(C)C1C=CN=CC=1.C(Cl)Cl>[Cl:17][C:18]1[N:23]=[CH:22][C:21]([S:24]([N:6]2[CH2:7][CH2:8][CH:3]([N:2]([CH3:9])[CH3:1])[CH2:4][CH2:5]2)(=[O:26])=[O:25])=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 417391N,N-Dimethylpiperidin-4-amineHCID 27927922-Chloro-5-pyridinesulfonyl chlorideHCID 21226129Dichloromethane methanol

Product 1

HCID 434306091-[(6-chloro-3-pyridinyl)sulfonyl]-N,N-dimethyl-4-PiperidinamineYield 94.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred ice-cooled solution of 4-(dimethylamino)piperidine (1.2 mL, 9.4 mmol), triethylamine (2.6 mL, 19 mmol), and 4-dimethylaminopyridine (0.012 g, 0.094 mmol) in DCM (18 mL) was added 6-chloropyridine-3-sulfonyl chloride (2.0 g, 9.4 mmol) in one portion. The resulting mixture was stirred at 0° C. for 1.5 h. Upon workup, the mixture was directly subjected to combi-flash column chromatography (methanol/DCM) to give compound 363 (2.7 g, 94% yield) as a white solid. LCMS-ESI (POS), M/Z, M+1: Found 304.0.

Sources & evidence

ORD record
ord-f167625d6b5544b1b197359d6bc6ec00
Source dataset
uspto-grants-2014_09
Patent number
US08841312B2

Linked notes

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