Potassium Carbonate → HCID 57494046, compound

HRID 2353155Notes

Reaction equation

HRID 2353155 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].[CH3:16][S:17]([CH2:20][CH2:21][CH2:22]OS(C1C=CC(C)=CC=1)(=O)=O)(=[O:19])=[O:18].C(=O)([O-])[O-].[K+].[K+]>CC#N>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]([CH2:22][CH2:21][CH2:20][S:17]([CH3:16])(=[O:19])=[O:18])[CH3:15])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15380702tert-Butyl 4-(methylamino)piperidine-1-carboxylateHCID 22732325(3-(Methylsulfonyl)propyl 4-methylbenzenesulfonate

Product 1

HCID 57494046HCID 57494046, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Amine preparation: Toluene-4-sulfonic acid 3-methylsulfanyl-propyl ester was prepared from 3-(methylthio)-1-propanol using standard conditions. Treatment with mCPBA in DCM yielded toluene-4-sulfonic acid 3-methanesulfonyl-propyl ester. A mixture of 4-methylamino-piperidine-1-carboxylic acid tert-butyl ester and toluene-4-sulfonic acid 3-methanesulfonyl-propyl ester was heated in MeCN in the presence of potassium carbonate to yield 4-[(3-methanesulfonyl-propyl)-methyl-amino]-piperidine-1-carboxylic acid tert-butyl ester. Treatment of this compound with HCl in DCM/MeOH yielded the desired amine, isolated as the hydrochloride salt.

Sources & evidence

ORD record
ord-bb6524c7e73846808f605ad6c59bb2db
Source dataset
uspto-grants-2010_07
Patent number
US07750002B2

Reaction notes

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