Benzenesulfonyl chloride → N-{2-[3'-(4-Methoxymethyl-phenyl)-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-yl]-ethyl}-N-methyl-benzenesulfonamide hydrochloride

HRID 553501Notes

Reaction equation

HRID 553501 reaction equation
[C:1]1([S:7]([Cl:10])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:11][O:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[C:21]([N:26]3[CH2:31][CH2:30][N:29]([CH2:32][CH2:33][NH:34][CH3:35])[CH2:28][CH2:27]3)=[N:22][CH:23]=[CH:24][N:25]=2)=[CH:16][CH:15]=1.N1CCOCC1>ClCCl>[ClH:10].[CH3:11][O:12][CH2:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[C:21]([N:26]3[CH2:27][CH2:28][N:29]([CH2:32][CH2:33][N:34]([CH3:35])[S:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)(=[O:9])=[O:8])[CH2:30][CH2:31]3)=[N:22][CH:23]=[CH:24][N:25]=2)=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8083MorpholineHCID 67367004{2-[3'-(4-Methoxymethyl-phenyl)-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-yl]-ethyl}-methyl-amine

Product 1

HCID 67368541N-{2-[3'-(4-Methoxymethyl-phenyl)-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-yl]-ethyl}-N-methyl-benzenesulfonamide hydrochlorideYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve benzenesulfonyl chloride (0.087 g, 0.49 mmol, 1.1 eq.) in dichloromethane (4 mL). Add {2-[3′-(4-methoxymethyl-phenyl)-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-yl]-ethyl}-methyl-amine (0.150 g, 0.440 mmol, 1 eq.). Add morpholine, polymer-bound (0.201 g, 0.490 mmol, 1.1 eq.). Stir at room temperature for 2 hr. Purify by SCX chromatography (column washed with methanol and extracted with 7N NH3/MeOH) to afford the free base of the title compound (0.202 g, 95% yield). MS (loop): m/z=482.3 [M+H].

Workup

  1. customPurify by SCX chromatography (column washed with methanol and extracted with 7N NH3/MeOH)

Sources & evidence

ORD record
ord-1f8d383c30d34e33b63cfd07a44af2e3
Source dataset
uspto-grants-2011_11
Patent number
US08048884B2

Reaction notes

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