Triethylamine → 1'-((4-Fluorophenyl)sulfonyl)spiro(1H-indene-1,4'-piperidine)

HRID 1534801Notes

Reaction equation

HRID 1534801 reaction equation
[NH:1]1[CH2:6][CH2:5][C:4]2([C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:8]=[CH:7]2)[CH2:3][CH2:2]1.C(N(CC)CC)C.[F:22][C:23]1[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1>C(Cl)Cl>[F:22][C:23]1[CH:28]=[CH:27][C:26]([S:29]([N:1]2[CH2:6][CH2:5][C:4]3([C:14]4[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=4)[CH:8]=[CH:7]3)[CH2:3][CH2:2]2)(=[O:31])=[O:30])=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 95884-Fluorobenzenesulfonyl chlorideHCID 10330052Spiro[indene-1,4'-piperidine]

Product 1

HCID 99975561'-((4-Fluorophenyl)sulfonyl)spiro(1H-indene-1,4'-piperidine)

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Spiro(1H-indene-1,4'-piperidine) (40 mg, 0.18 mmol) was suspended in CH2Cl2 (2 ml) and treated with triethylamine (52.6 μl, 0.378 mmol) followed by 4-fluorobenzenesulfonyl chloride (38.6 mg, 0.198 mmol). The reaction was stirred 1 hr at ambient temperature and chromatographed on a silica gel column eluted with 20% hexane in CH2Cl2. The product fractions were evaporated to dryness in vacuo and the residue crystallized from ether to provide the title compound: (mp 169°-174°).

Workup

  1. customchromatographed on a silica gel column
  2. washeluted with 20% hexane in CH2Cl2
  3. customThe product fractions were evaporated to dryness in vacuo
  4. customthe residue crystallized from ether

Sources & evidence

ORD record
ord-591497055d644a7d8dc2298b0ac91b99
Source dataset
uspto-grants-1992_02
Patent number
US05091387

Reaction notes

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