4-Toluenesulfonyl chloride → HCID 23150320, compound

HRID 657643Notes

Reaction equation

HRID 657643 reaction equation
[OH:1][CH2:2][CH2:3][C:4]#[C:5][C:6]1[CH:21]=[CH:20][C:9]([O:10][CH2:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:8][CH:7]=1.C(N(CC)CC)C.[S:29](Cl)([C:32]1[CH:38]=[CH:37][C:35]([CH3:36])=[CH:34][CH:33]=1)(=[O:31])=[O:30]>C(#N)C.CN(C)C1C=CN=CC=1>[S:29]([O:1][CH2:2][CH2:3][C:4]#[C:5][C:6]1[CH:21]=[CH:20][C:9]([O:10][CH2:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:8][CH:7]=1)([C:32]1[CH:38]=[CH:37][C:35]([CH3:36])=[CH:34][CH:33]=1)(=[O:31])=[O:30]

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 57672010HCID 57672010, compound

Product 1

HCID 23150320HCID 23150320, compoundYield 81,975.102%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of 1-{3-[4-(4-hydroxybut-1-yn-1-yl)phenoxy]propyl}piperidine (393 mg) in acetonitrile (10 mL) are added successively triethylamine (0.446 mL), 4-dimethylaminopyridine (18 mg) and tosyl chloride (617 mg). The mixture is stirred overnight at room temperature, concentrated under reduced pressure and purified by chromatography over silica gel to give 495 g of 1-{3-[4-(4-tosyloxybut-1-yn-1-yl)phenoxy]propyl}piperidine.

Workup

  1. concentrationconcentrated under reduced pressure
  2. custompurified by chromatography over silica gel

Sources & evidence

ORD record
ord-7730397e1b8849d9b1d7fe12fdd34a0c
Source dataset
uspto-grants-2011_12
Patent number
US08076329B2

Reaction notes

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