4-Toluenesulfonyl chloride → HCID 57850571, compound

HRID 736656Notes

Reaction equation

HRID 736656 reaction equation
[CH2:1]([N:8]1[CH2:13][CH:12]=[C:11]([CH2:14][CH2:15][OH:16])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.C(N(CC)CC)C>ClCCl.CN(C1C=CN=CC=1)C>[CH2:1]([N:8]1[CH2:9][CH:10]=[C:11]([CH2:14][CH2:15][O:16][S:23]([C:20]2[CH:21]=[CH:22][C:17]([CH3:27])=[CH:18][CH:19]=2)(=[O:25])=[O:24])[CH2:12][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 21955250HCID 21955250, compound

Product 1

HCID 57850571HCID 57850571, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-(1-benzyl-1,2,3,6-tetrahydro-pyridin-4-yl)ethanol (0.822 g, 4.09 mmol) (J. Med. Chem. 1990, 33, 3133) in dichloromethane was added p-toluene sulfonyl chloride (1.71 g, 9.00 mmol) and triethyl amine (2.3 mL, 16.4 mmol) and DMAP (0.050 g, 0.41 mmol) at room temperature and stirring continued at rt for 3 h. The reaction mixture was diluted with dichloromethane and washed with aq NaHCO3 (10% W/V) solution, followed by saturated NaCl solution. The organic layer was dried (Na2SO4), filtered and solvent was evaporated to dryness. The product was flash chromatographed over silica gel using gradient of 0-10% methanol in dichloromethane. 1H NMR (CDCl3) δ 7.77 (d, 8.4 Hz, 2H), 7.34-7.30 (m, 5H), 7.26 (m, 1H), 5.36 (m, 1H), 4.09 (t, J=6.8 Hz, 2H), 3.54 (s, 2H), 2.92-2.88 (m, 2H), 2.50 (t, J=5.6 Hz, 2H), 2.44 (s, 3H), 2.31 (brt, J=6.8 Hz, 2H), 2.20-1.84 (m, 2H).

Workup

  1. washwashed with aq NaHCO3 (10% W/V) solution
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. customsolvent was evaporated to dryness
  5. customchromatographed over silica gel using gradient of 0-10% methanol in dichloromethane

Sources & evidence

ORD record
ord-98cb01acb11a46819fedb709b9ebee58
Source dataset
uspto-grants-2009_09
Patent number
US07595401B2

Reaction notes

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