Hydrochloric Acid → HCID 54507608, compound

HRID 1419891Notes

Reaction equation

HRID 1419891 reaction equation
CS(Cl)(=O)=O.Cl.NC1C=CC(OCC(O)CN2CCC(CC3C=CC=CC=3)(O)CC2)=CC=1.Cl.Cl.[CH2:35]([C:42]1([OH:64])[CH2:47][CH2:46][N:45]([CH2:48][CH:49]([OH:63])[CH2:50][O:51][C:52]2[CH:57]=[CH:56][C:55]([NH:58][S:59]([CH3:62])(=[O:61])=[O:60])=[CH:54][CH:53]=2)[CH2:44][CH2:43]1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>C(Cl)Cl.N1C=CC=CC=1.[Cl-].[Na+].O.C(O)C.C(OC)(C)(C)C.O>[CH2:35]([C:42]1([OH:64])[CH2:43][CH2:44][N:45]([CH2:48][CH:49]([OH:63])[CH2:50][O:51][C:52]2[CH:53]=[CH:54][C:55]([NH:58][S:59]([CH3:62])(=[O:61])=[O:60])=[CH:56][CH:57]=2)[CH2:46][CH2:47]1)[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

11

Reactant 4

HCID 313Hydrochloric AcidHCID 31297Methanesulfonyl chlorideHCID 70046718HCID 70046718, compoundHCID 70048314HCID 70048314, compound

Product 1

HCID 54507608HCID 54507608, compound

Reagents, catalysts & solvents 6

HCID 702EthanolSolventHCID 962WaterSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolventHCID 15413tert-Butyl methyl etherSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Methane sulfonylchloride (0.105 ml, 1.4 mmol) was added to a suspension of (RS)-1-[3-(4-amino-phenoxy)-2-hydroxy-propyl]-4-benzyl-piperidin-4-ol hydrochloride (0.5 g, 1.3 mmol) in CH2Cl2 (10 ml) and pyridine (5 ml) at room temperature. The mixture was stirred at room temperature overnight, water (15 ml) and brine (15 ml) were added and the mixture was extracted with CH2Cl2 (5×25 ml). The organic phases were pooled, dried with Na2SO4 and the solvent evaporated. The residue was chromatographed over silica gel (ethyl acetate-MeOH, 96:4) to give a colorless oil which was dissolved in ethanol (2 ml). 1.1 Equivalent of ethanolic HCl and t-butylmethylether (50 ml) were added to give (RS)-N-{4-[3-(4-benzyl-4-hydroxy-piperidin-1-yl)-2-hydroxy-propoxy]-phenyl}-methanesulfonamide hydrochloride (0.24 g, 38%) as colorless solid mixture of the E/Z isomers, m.p. >230° C. dec and MS: m/e =435.4 (M+H+).

Workup

  1. extractionthe mixture was extracted with CH2Cl2 (5×25 ml)
  2. dry with materialdried with Na2SO4
  3. customthe solvent evaporated
  4. customThe residue was chromatographed over silica gel (ethyl acetate-MeOH, 96:4)
  5. customto give a colorless oil which
  6. customto give

Sources & evidence

ORD record
ord-9604818b942f499da444042144a85efa
Source dataset
uspto-grants-1999_03
Patent number
US05889026

Reaction notes

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