4-Toluenesulfonyl chloride → HCID 9797987, compound

HRID 1534787Notes

Reaction equation

HRID 1534787 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][C:5]2([C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[CH:8]2)[CH2:4][CH2:3]1.[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1>C(Cl)Cl.C(N(CC)CC)C>[CH3:26][C:16]1[CH:21]=[CH:20][C:19]([S:22]([N:2]2[CH2:7][CH2:6][C:5]3([C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[CH:9]=[CH:8]3)[CH2:4][CH2:3]2)(=[O:24])=[O:23])=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 22509344Spiro[indene-1,4'-piperidine] hydrochloride

Product 1

HCID 9797987HCID 9797987, compound

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 6344DichloromethaneSolvent

Procedure

Spiro(1H-indene-1,4'-piperidine)hydrochloride (65 mg, 293 μmol) and p-toluenesulfonyl chloride (61.9 mg, 325 μmol) were combined in CH2Cl2 and treated with triethylamine (2 drops). The mixture was stirred at ambient temperature for 1 hour, then poured onto a silica gel column and eluted with 35% hexane in CH2Cl2. The product fractions were combined and evaporated to dryness in vacuo to provide the title compound which was crystallized from ether, filtered and dried in vacuo overnight at ambient temperature: (m.p. 168°-170°).

Workup

  1. additionpoured onto a silica gel column
  2. washeluted with 35% hexane in CH2Cl2
  3. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-82ce34e5fe924ed994c5581fe0941e61
Source dataset
uspto-grants-1992_02
Patent number
US05091387

Reaction notes

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