4-Nitrobenzenesulfonyl chloride → HCID 86747662, compound

HRID 487319Notes

Reaction equation

HRID 487319 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH:10]([CH3:14])[N:9]([CH2:15][CH2:16][NH:17]C(=O)C1C=CC([N+]([O-])=O)=CC=1)[CH2:8][CH2:7]2.[N+:29]([C:32]1[CH:37]=[CH:36][C:35]([S:38]([Cl:41])(=[O:40])=[O:39])=[CH:34][CH:33]=1)([O-:31])=[O:30]>>[ClH:41].[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH:10]([CH3:14])[N:9]([CH2:15][CH2:16][NH:17][S:38]([C:35]1[CH:34]=[CH:33][C:32]([N+:29]([O-:31])=[O:30])=[CH:37][CH:36]=1)(=[O:39])=[O:40])[CH2:8][CH2:7]2

Participants

3

Reactant 2

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 19093932HCID 19093932, compound

Product 1

HCID 86747662HCID 86747662, compound

Procedure

The title compound was prepared by Method A using 2-(2-aminoethyl)-1,2,3,4-tetrahydro-6-methoxy-1-methylisoquinoline (described in Example 178) and 4-nitrobenzenesulfonyl chloride to produce the desired product in 100% yield. This material was purified by flash silica gel chromatography using 10-100% EtOAc in hexane. The material obtained was treated with HCl/2-propanol (1.1 eq) to afford a beige solid; mp 167°-172° C.; IR (KBr) 1611, 1531,1507,1443,1347,1309,1248,1232,1168,1092,1029,852,745,739 and 607 cm-1.

Sources & evidence

ORD record
ord-c70e8cccfc194f63b415c095bf89121a
Source dataset
uspto-grants-1994_03
Patent number
US05294621

Reaction notes

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