Dimethylamine → HCID 66698090, compound

HRID 1256554Notes

Reaction equation

HRID 1256554 reaction equation
[CH:1]([S:3]([N:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[CH2:8][CH2:7]1)(=[O:5])=[O:4])=[CH2:2].[CH3:22][NH:23][CH3:24]>C1COCC1.O>[CH3:22][N:23]([CH3:24])[CH2:2][CH2:1][S:3]([N:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[CH2:8][CH2:7]1)(=[O:5])=[O:4]

Participants

5

Reactant 2

HCID 674DimethylamineHCID 666980981246203-64-4

Product 1

HCID 66698090HCID 66698090, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of the above vinylsulfonamide (3.10 g, 10 mmol) in 20 mL of THF was treated with an excess (10 mL, 80 mmol) of 40% aqueous dimethylamine. After 5 min, the mixture was diluted with water to give 3.09 g (87% yield) of benzyl 4-{[2-(dimethyl-amino)ethyl]sulfonyl}-1-piperazinecarboxylate as a white solid: mp (aq. MeOH) 101-103° C.; 1H NMR (CDCl3) δ 7.40-7.30 (m, 5H), 5.15 (s, 2H), 3.59 (m, 4H), 3.26 (m, 4H), 3.07 (dd J=8.1, 6.4 Hz, 2H), 2.74 (dd, J=8.0, 6.4 Hz, 2H), 2.25 (s, 6H); Anal. Calcd. for C16H25N3O4S: C, 54.1; H, 7.1; N, 11.8. Found: C, 53.8; H, 6.9; N, 11.8%.

Sources & evidence

ORD record
ord-451d4048688e4309b5c1e07bdf2e135a
Source dataset
uspto-grants-2013_06
Patent number
US08461158B2

Reaction notes

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