1-Naphthalenesulfonyl chloride → Methyl 1-(naphthalen-1-ylsulfonyl)piperidine-4-carboxylate

HRID 2356213Notes

Reaction equation

HRID 2356213 reaction equation
[NH:1]1[CH2:10][CH2:9][CH:4]([C:5]([O:7][CH3:8])=[O:6])[CH2:3][CH2:2]1.[C:11]1([S:21](Cl)(=[O:23])=[O:22])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[C:11]1([S:21]([N:1]2[CH2:10][CH2:9][CH:4]([C:5]([O:7][CH3:8])=[O:6])[CH2:3][CH2:2]2)(=[O:23])=[O:22])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 665601-Naphthalenesulfonyl chlorideHCID 424914Methyl isonipecotate

Product 1

HCID 11950392Methyl 1-(naphthalen-1-ylsulfonyl)piperidine-4-carboxylateYield 73.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

Methyl isonipecotate (1.0 g, 6.9 mmol), 1-naphthalenesulfonyl chloride (1.58 g, 6.9 mmol) and DMAP (0.17 g, 1.4 mmol) were dissolved in pyridine (10 mL). After stirring overnight, the reaction mixture was concentrated in vacuo, diluted with water (15 mL) and extracted into methylene chloride (3×10 mL). The combined organic extracts were dried over anhydrous sodium sulfate and concentrated in vacuo. The resulting yellow oil was purified by column chromatography on SiO2 eluted with hexanes/ethyl acetate (1:1) to yield 1.7 g (73%)of the title compound as a white foam. 1H NMR (400 MHz, Chloroform-d) δ, ppm: 1.67-1.77 (m, 2 H), 1.93 (dd, J=13.64, 3.79 Hz, 2 H), 2.25-2.34 (m, 1 H), 2.68-2.77 (m, 2 H), 3.63 (s, 3 H), 3.74 (ddd, J=12.51, 3.66, 3.54 Hz, 2 H), 7.56-7.66 (m, 3 H), 7.92 (d, J=9.35 Hz, 1 H), 8.07 (d, J=8.34 Hz, 1 H), 8.21 (d, J=7.33 Hz, 1 H), 8.71 (d, J=8.08 Hz, 1 H); ESI-MS: m/z 334.3 (M+H)+.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. additiondiluted with water (15 mL)
  3. extractionextracted into methylene chloride (3×10 mL)
  4. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resulting yellow oil was purified by column chromatography on SiO2
  7. washeluted with hexanes/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-f0f56f5c517544fab55c712b2acc28c2
Source dataset
uspto-grants-2010_07
Patent number
US07759339B2

Reaction notes

Loading…