4-Chlorobenzenesulfonyl chloride → Allyl-{4-[1-(4-chloro-benzenesulfonyl)-1,2,3,4-tetrahydro-quinolin-6-yloxy]-but-2-enyl}-methyl-amine

HRID 49481Notes

Reaction equation

HRID 49481 reaction equation
[CH2:1]([N:4]([CH3:20])[CH2:5][CH:6]=[CH:7][CH2:8][O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH2:15][CH2:14][CH2:13]2)[CH:2]=[CH2:3].CCN(C(C)C)C(C)C.[Cl:30][C:31]1[CH:36]=[CH:35][C:34]([S:37](Cl)(=[O:39])=[O:38])=[CH:33][CH:32]=1>C(Cl)Cl>[CH2:1]([N:4]([CH2:5][CH:6]=[CH:7][CH2:8][O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]([S:37]([C:34]1[CH:35]=[CH:36][C:31]([Cl:30])=[CH:32][CH:33]=1)(=[O:39])=[O:38])[CH2:15][CH2:14][CH2:13]2)[CH3:20])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 69514787Allyl-methyl-[4-(1,2,3,4-tetrahydro-quinolin-6-yloxy)-but-2-enyl]-amine

Product 1

HCID 69514870Allyl-{4-[1-(4-chloro-benzenesulfonyl)-1,2,3,4-tetrahydro-quinolin-6-yloxy]-but-2-enyl}-methyl-amineYield 78.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneCatalyst

Procedure

To 54 mg (0.2 mmol) Allyl-methyl-[4-(1,2,3,4-tetrahydro-quinolin-6-yloxy)-but-2-enyl]-amine in 2 ml CH2Cl2 3 drops of Huenig's base and 527 mg (0.25 mmol) 4-chlorobenzene sulfonylchloride were added. The solution was stirred at RT for 2 h, concentrated and purified by column chromatography on silica gel with CH2Cl2/MeOH 19:1 to yield 70 mg (78%) Allyl-{4-[1-(4-chloro-benzenesulfonyl)-1,2,3,4-tetrahydro-quinolin-6-yloxy]-but-2-enyl}-methyl-amine as yellow oil, MS: 447 (MH+, 1Cl).

Workup

  1. concentrationconcentrated
  2. custompurified by column chromatography on silica gel with CH2Cl2/MeOH 19:1

Sources & evidence

ORD record
ord-ceb076853049454ab52bc498979c69a2
Source dataset
uspto-grants-2004_03
Patent number
US06706751B2

Reaction notes

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