4-Toluenesulfonyl chloride → HCID 69422321, compound

HRID 1178872Notes

Reaction equation

HRID 1178872 reaction equation
Cl.Cl.[CH3:3][NH:4][C@H:5]1[CH2:9][CH2:8][C@@H:7]([N:10]2[CH2:15][CH2:14][CH:13]([CH3:16])[CH2:12][CH2:11]2)[CH2:6]1.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23]([Cl:26])(=[O:25])=[O:24])=[CH:19][CH:18]=1>ClCCl.[OH-].[Na+]>[ClH:26].[CH3:27][C:17]1[CH:22]=[CH:21][C:20]([S:23]([N:4]([CH3:3])[C@H:5]2[CH2:9][CH2:8][C@@H:7]([N:10]3[CH2:15][CH2:14][CH:13]([CH3:16])[CH2:12][CH2:11]3)[CH2:6]2)(=[O:25])=[O:24])=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 69419848HCID 69419848, compound

Product 1

HCID 69422321HCID 69422321, compoundYield 89.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of cis-1-methylamino-3-(4-methylpiperidin-1-yl)cyclopentane dihydrochloride (24.5 mg, 0.091 mmol) and 4-toluenesulfonyl chloride (27.9 mg, 0.146 mmol) in dichloromethane (2 ml) and 1M aqueous sodium hydroxide (2 ml) was rapidly stirred at room temperature overnight (22 hours). The phases were separated and the aqueous extracted with more dichloromethane (5 ml). The combined organics were dried (MgSO4) and evaporated. The residue was dissolved in methanol-ethyl acetate and treated with excess 1M hydrogen chloride in diethyl ether. Recrystallization of the resulting solid from methanol-ethyl acetate gave the title compound (31.5 mg, 89%) as a white solid; δH (400 MHz, CD3OD) 1.00 (3H, d, J 6.1 Hz), 1.43 (2H, m), 1.62-1.83 (5H, m), 1.91 (2H, m), 2.04-2.18 (2H, m), 2.43 (3H, s), 2.77 (3H, s), 2.89 (2H, m), 3.50 (3H, m), 4.41 (1H, m), 7.40 (2H, d, J 8.5 Hz), 7.71 (2H, d, J 8.5 Hz); m/z (ES+) 351 ([M+H]+, 100%).

Workup

  1. customThe phases were separated
  2. extractionthe aqueous extracted with more dichloromethane (5 ml)
  3. dry with materialThe combined organics were dried (MgSO4)
  4. customevaporated
  5. dissolutionThe residue was dissolved in methanol-ethyl acetate
  6. additiontreated with excess 1M hydrogen chloride in diethyl ether
  7. customRecrystallization of the resulting solid from methanol-ethyl acetate

Sources & evidence

ORD record
ord-5049ae0f85f74efca608affabda623b5
Source dataset
uspto-grants-2007_10
Patent number
US07276607B2

Reaction notes

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