2,6-Lutidine → HCID 178483624, compound

HRID 967176Notes

Reaction equation

HRID 967176 reaction equation
Cl.[CH3:2][NH:3][CH2:4][CH2:5][C@H:6]1[CH2:11][CH2:10][C@H:9](/[CH:12]=[CH:13]/[CH2:14]O)[CH2:8][CH2:7]1.[S:16](Cl)([OH:19])(=O)=[O:17].[F:21][C:22]([F:30])([F:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(C(C)C)CC)(C)C.CS([Cl:44])(=O)=O.N1C(C)=CC=CC=1C>ClCCl>[Cl:44][CH2:14]/[CH:13]=[CH:12]/[C@H:9]1[CH2:10][CH2:11][C@H:6]([CH2:5][CH2:4][N:3]([CH3:2])[S:16]([C:26]2[CH:27]=[CH:28][C:23]([C:22]([F:30])([F:29])[F:21])=[CH:24][CH:25]=2)(=[O:19])=[O:17])[CH2:7][CH2:8]1

Participants

7

Reactant 5

HCID 79372,6-LutidineHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 222941704-Trifluoromethyl-benzene sulfochlorideHCID 178483629HCID 178483629, compound

Product 1

HCID 178483624HCID 178483624, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In analogy to the sequence described in examples 17.3 and 17.4, trans-3-[4-(2-methylamino-ethyl)-cyclohexyl]-(E)-prop-2-en-1-ol HCl was reacted with 4-trifluoromethyl-benzene sulfochloride in dichloromethane in the presence of diisopropyl ethyl amine followed by treatment with methane sulfonylchloride and 2,6-lutidine in dichloromethane to yield trans-N-{2-[4-(3-chloro-(E)-propenyl)-cyclohexyl]-ethyl}-N-methyl-4-trifluoromethyl-benzenesulfonamide as colorless viscous oil, MS: 424 (MH+, 1Cl).

Sources & evidence

ORD record
ord-a9f139d8336e4eb587d08d396e0cfbb6
Source dataset
uspto-grants-2005_10
Patent number
US06953806B2

Reaction notes

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