Isethionic Acid → HCID 23294554, compound

HRID 1955244Notes

Reaction equation

HRID 1955244 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][O:16][C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[C:22]([O:27]CC4C=CC=CC=4)[CH:23]=3)[CH:18]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(CCO)(O)(=O)=O>[Pd].CO.O1CCCC1>[CH2:1]([CH:8]1[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][O:16][C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[CH:23]=[C:22]([OH:27])[CH:21]=[CH:20]3)[CH2:12][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 7866Isethionic AcidHCID 23294431HCID 23294431, compound

Product 1

HCID 23294554HCID 23294554, compoundYield 95.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of of 4-benzyl-1-[2-(6-benzyloxy-naphthalen-2-yloxy)-ethyl]-piperidine (0.67 g, 1.48 mmol) and 20% palladium on carbon (0.06 g) in methanol (8 ml) and tetrahydrofuran (8 ml) was shaken on a Parr hydrogenation apparatus under a hydrogen atmosphere (50 psi) for 20 h. After removal of the catalyst, the filtrate was evaporated and the white solid (0.51 g, 95%) was dissolved in tetrahydofuran (5 ml). A solution of isethionic acid in methanol (4.6 ml, 1.28 mmol) was added, and the solid precipitate was filtered off. The solid was washed with tetrahydofuran, and dried in vacuo overnight to give the title compound (0.51 g, 82%), mp139-141° C. Analysis calculated for C24H27NO2 ·C2H6O4S: C, 64.04; H, 6.82; N, 2.87; S, 6.58. Found: C, 63.88; H, 6.77; N, 2.70; S, 6.60.

Workup

  1. customAfter removal of the catalyst
  2. customthe filtrate was evaporated
  3. dissolutionthe white solid (0.51 g, 95%) was dissolved in tetrahydofuran (5 ml)
  4. filtrationthe solid precipitate was filtered off
  5. washThe solid was washed with tetrahydofuran
  6. customdried in vacuo overnight

Sources & evidence

ORD record
ord-bf4091be5f8a4479a326d33eae7e9054
Source dataset
uspto-grants-2000_09
Patent number
US06124323

Reaction notes

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