4-(Piperazin-1-yl)benzene-1-sulfonamide → (S)-(-)-3-Bromo-4-[4-[2-(6-bromoisochroman-1-yl)ethyl]piperazin-1-yl]benzenesulfonamide

HRID 368868

Reaction equation

HRID 368868 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]([CH2:12][CH2:13]O)[O:7][CH2:6][CH2:5]2.Cl.[Br:16][C:17]1[CH:18]=[C:19]([S:29]([NH2:32])(=[O:31])=[O:30])[CH:20]=[CH:21][C:22]=1[N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.BrC1C=C(OC)C=CC=1N1CCNCC1.N1(C2C=CC(S(N)(=O)=O)=CC=2)CCNCC1>>[Br:16][C:17]1[CH:18]=[C:19]([S:29]([NH2:32])(=[O:30])=[O:31])[CH:20]=[CH:21][C:22]=1[N:23]1[CH2:28][CH2:27][N:26]([CH2:13][CH2:12][C@H:8]2[C:9]3[C:4](=[CH:3][C:2]([Br:1])=[CH:11][CH:10]=3)[CH2:5][CH2:6][O:7]2)[CH2:25][CH2:24]1

Participants

5

Reactant 4

HCID 9018974-(Piperazin-1-yl)benzene-1-sulfonamideHCID 232888302-(6-Bromoisochroman-1-yl)ethanolHCID 232888383-Bromo-4-(piperazin-1-yl)-benzenesulfonamide hydrochlorideHCID 232889281-(2-Bromo-4-methoxyphenyl)piperazine

Product 1

HCID 54523419(S)-(-)-3-Bromo-4-[4-[2-(6-bromoisochroman-1-yl)ethyl]piperazin-1-yl]benzenesulfonamide

Procedure

Following the general procedure of EXAMPLE 49 and making non-critical variations, 2-(6-bromoisochroman-1-yl)ethanol (LXXIX, 0.399 g) and 3-bromo-4-(piperazin-1-yl)- benzenesulfonamide hydrochloride (VIII, Chart C, 0.544 g; prepared by the method of EXAMPLE 37 but using 4-(piperazin-1-yl)benzenesulfonamide (IV) in place of 1-(4-methoxyphenyl)piperazine) are combined to give the title compound; mp 206-208°; MS (m/z) 557 and 559; IR (mineral oil) 1165, 1338, 1450, 616, 1586 and 731 cm-1.

Workup

  1. customprepared by the method of EXAMPLE 37

Sources & evidence

ORD record
ord-73d7d63e4ffc4b4b81b5d8590bff1598
Source dataset
uspto-grants-2000_10
Patent number
US06133446

Linked notes

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