4-Toluenesulfonyl chloride → HCID 86584029, compound

HRID 1861763Notes

Reaction equation

HRID 1861763 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][OH:17])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18]1([CH3:28])[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1>C(Cl)Cl>[CH2:1]([CH:8]1[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][CH2:16][O:17][S:24]([C:21]2[CH:22]=[CH:23][C:18]([CH3:28])=[CH:19][CH:20]=2)(=[O:26])=[O:25])[CH2:12][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 12972964HCID 12972964, compound

Product 1

HCID 86584029HCID 86584029, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
25 °C

Procedure

To a solution of 4-benzyl-1-(3-hydroxypropyl)piperidine (1.0 g, 4.29 mmol) in CH2Cl2 (20 mL) were added TEA (1.2 mL, 8.57 mmol) and dropwise a solution of p-toluenesulfonyl chloride (1.22 g, 6.4 mmol) in CH2Cl2 (10 mL). The resulting solution was stirred at 25° C. for 2 h then diluted with CH2Cl2 (60 mL) and washed with NH4Cl (2×100 mL), dried and concentrated in vacuum to afford the crude intermediate, which was purified by trituration with EtOAc (10 mL) to give the title compound as a white solid (0.63 g, 38%), mp 143-145° C. 1H-NMR (CDCl3): 1.2-1.45 (m, 2H), 1.65-1.85 (m, 3H), 2.319 (s, 3H), 2.502 (d, J=7.2Hz, 2H), 2.6-2.8 (m, 2H), 3.338 (t, J=12.6Hz, 2H), 3.875 (d, J=12.6, 2H), 4.277 (t, J=8.1Hz, 2H), 4.421 (t, J=8.4Hz, 2H), 7.064 (d, J 7.2Hz, 2H), 7.122 (d, J=7.8Hz, 2H), 7.15-7.30 (m, 3H), 7.76 (d, J=7.8Hz, 2H).

Workup

  1. washwashed with NH4Cl (2×100 mL)
  2. customdried
  3. concentrationconcentrated in vacuum
  4. customto afford the crude intermediate, which
  5. customwas purified by trituration with EtOAc (10 mL)

Sources & evidence

ORD record
ord-9132ffe230e04d81a1b9013c16bef46f
Source dataset
uspto-grants-2003_03
Patent number
US06534522B2

Reaction notes

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