Triethylamine → 1-(Methylsulfonyl)spiro[indoline-3,4'-piperidine] hydrochloride

HRID 1735474Notes

Reaction equation

HRID 1735474 reaction equation
C[N:2]1[CH2:7][CH2:6][C:5]2([C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][CH2:8]2)[CH2:4][CH2:3]1.C(N(CC)CC)C.[CH3:23][S:24]([Cl:27])(=[O:26])=[O:25].C(=O)(O)[O-].[Na+]>ClCCl>[ClH:27].[CH3:23][S:24]([N:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:5]2([CH2:6][CH2:7][NH:2][CH2:3][CH2:4]2)[CH2:8]1)(=[O:26])=[O:25]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 128015871'-Methylspiro[indoline-3,4'-piperidine]

Product 1

HCID 219560841-(Methylsulfonyl)spiro[indoline-3,4'-piperidine] hydrochlorideYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.20 g (5.8mmol) of 1'-methyl-1,2-dihydro-spiro[3H-indole-3,4'-piperdine](prepared as described in H. Ong et al J. Med. Chem. 1983, 23, 981-986) in 20 mL of dry dichloromethane at 0° C. was added triethylamine (0.90 mL; 6.4 mmol) and methanesulfonyl chloride (0.49 mL; 6.35 mmol) and stirred for 30 min. The reaction mixture was poured into 15 mL of saturated aqueous sodium bicarbonate solution and extracted with dichloromethane (2×10 mL). The combined organics were washed with brine (20 mL), dried over anhydrous potassium carbonate, filtered and the solvent removed under reduced pressure to yield 1.44 g of the methanesulfonamide derivative as pale yellow oil which was used without purification.

Workup

  1. extractionextracted with dichloromethane (2×10 mL)
  2. washThe combined organics were washed with brine (20 mL)
  3. dry with materialdried over anhydrous potassium carbonate
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-c89783633f0347b0bfbe33896ccbf9d4
Source dataset
uspto-grants-1996_07
Patent number
US05536716

Reaction notes

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