Methanesulfonyl chloride → Tert-butyl 4-(methylsulfonyl)piperazine-1-carboxylate

HRID 1972302Notes

Reaction equation

HRID 1972302 reaction equation
[Cl-].[CH3:2][S:3]([N:6]1[CH2:11][CH2:10][NH2+:9][CH2:8][CH2:7]1)(=[O:5])=[O:4].[C:12]([O:16][C:17](N1CCNCC1)=[O:18])([CH3:15])([CH3:14])[CH3:13].CS(Cl)(=O)=O>>[CH3:2][S:3]([N:6]1[CH2:11][CH2:10][N:9]([C:17]([O:16][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:18])[CH2:8][CH2:7]1)(=[O:5])=[O:4]

Participants

4

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 143452tert-Butyl piperazine-1-carboxylateHCID 68731830HCID 68731830, compound

Product 1

HCID 4496004Tert-butyl 4-(methylsulfonyl)piperazine-1-carboxylate

Procedure

Scheme 2 shows the synthesis of 4-(methylsulfonyl)piperazin-1-ium chloride 8 starting by N-sulfonylation of 1-(tert-butoxycarbonyl)piperazine 6 (BOC-piperazine) with methanesulfonyl chloride to give tert-butyl 4-(methylsulfonyl)piperazine-1-carboxylate 7 which was treated with aqueous hydrogen chloride solution in 1,4-dioxane to give 8.

Sources & evidence

ORD record
ord-8d48cd99c5ba47ea8001ba6b5019816b
Source dataset
uspto-grants-2013_04
Patent number
US08431694B1

Reaction notes

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