Water → HCID 58828636, compound

HRID 1711403Notes

Reaction equation

HRID 1711403 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:25][S:26]([C:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31][CH:30]=1)(=[O:28])=[O:27].CC(C)([O-])C.[K+].O>C1COCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:16]=[CH:17][C:18]([N+:21]([O-:23])=[O:22])=[C:19]([CH2:25][S:26]([C:29]3[C:38]4[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=4)[CH:32]=[CH:31][CH:30]=3)(=[O:27])=[O:28])[CH:20]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 117366081-((Chloromethyl)sulfonyl)naphthaleneHCID 12094715HCID 12094715, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 58828636HCID 58828636, compoundYield 47.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1-benzyl-4-(4-nitrophenoxy)piperidine (3.00 g, 9.60 mmol) and 1-chloromethanesulfonyl-naphthalene (2.35 g, 9.76 mmol) in THF was chilled in an ice bath, treated dropwise with 1.0 M potassium tert-butoxide in THF (20 mL, 20 mmol), stirred at ambient temperature for 1 hour, 20 minutes under nitrogen, poured into water and extracted with ethyl acetate. The extracts were combined, washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The resultant residue was purified by flash chromatography using 40-80% ethyl acetate in hexane to give 1-benzyl-4-[3-(naphthalene-1-sulfonylmethyl)-4-nitro-phenoxy]-piperidine as a brown gum/foam, 2.36 g (47.6% yield), Mass spectrum (+EI, [M+H]+) m/z 517. 1HNMR (500 MHz, DMSO-d6): δ8.44-8.47 (m, 1H), 8.28 (d, 1H, J=8.17 Hz), 8.06-8.09 (m, 1H), 7.91-7.96 (m, 2H), 7.59-7.68 (m, 3H), 7.20-7.32 (m, 5H), 7.03 (dd, 1H, J=9.15 Hz and 2.80 Hz), 6.62 (d, 1H, J=2.81 Hz), 5.24 (s, 2H), 4.07-4.10 (m, 1H), 3.44 (s, 2H), 2.49-2.53 (m, 2H), 2.05-2.09 (m, 2H), 1.65-1.69 (m, 2H), 1.38-1.46 ppm (m, 2H).

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resultant residue was purified by flash chromatography

Sources & evidence

ORD record
ord-8aba8b30b3f44814a1c0bb1d183e68ea
Source dataset
uspto-grants-2010_09
Patent number
US07790751B2

Reaction notes

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