Potassium Iodide → 4-(3-Morpholin-4-yl-propane-1-sulfonyl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 2365186Notes

Reaction equation

HRID 2365186 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([S:14]([CH2:17][CH2:18][CH2:19]Cl)(=[O:16])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC#N>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([S:14]([CH2:17][CH2:18][CH2:19][N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)(=[O:16])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 8083MorpholineHCID 11430Potassium CarbonateHCID 227098904-tert-Butoxycarbonyl-1-[(3-chloro-1-propyl)sulfonyl]piperazine

Product 1

HCID 574939734-(3-Morpholin-4-yl-propane-1-sulfonyl)-piperazine-1-carboxylic acid tert-butyl esterYield 89%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-(3-Chloro-propane-1-sulfonyl)-piperazine-1-carboxylic acid tert-butyl ester (4.64 g), morpholine (1.6 mL, 1.3 eq.), potassium carbonate (2.17 g, 1.1 eq.), potassium iodide (1.11 g, 0.47 eq.) were refluxed together in dry MeCN (100 mL) overnight. Concentration in vacuo, then aqueous work-up followed by flash chromatography gave 4-(3-morpholin-4-yl-propane-1-sulfonyl)-piperazine-1-carboxylic acid tert-butyl ester (89%). Treatment with 2M HCl in ether gave product (4.46 g).

Workup

  1. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-2b27d9d7190849a5bf20cf239b5ae4cf
Source dataset
uspto-grants-2014_04
Patent number
US08697693B2

Reaction notes

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