Acetic Acid → 1-Sec-butyl-4-(3-methanesulfonyl-phenyl)piperidine

HRID 1483900Notes

Reaction equation

HRID 1483900 reaction equation
Cl.[CH3:2][S:3]([C:6]1[CH:7]=[C:8]([CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[CH:9]=[CH:10][CH:11]=1)(=[O:5])=[O:4].C(O)(=O)C.[CH3:22][C:23](=O)[CH2:24][CH3:25].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH:23]([N:15]1[CH2:16][CH2:17][CH:12]([C:8]2[CH:9]=[CH:10][CH:11]=[C:6]([S:3]([CH3:2])(=[O:5])=[O:4])[CH:7]=2)[CH2:13][CH2:14]1)([CH2:24][CH3:25])[CH3:22]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6569Methyl Ethyl KetoneHCID 5049666Sodium triacetoxyborohydrideHCID 223978414-(3-(Methylsulfonyl)phenyl)piperidine hydrochloride

Product 1

HCID 223978211-Sec-butyl-4-(3-methanesulfonyl-phenyl)piperidine

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

4-(3-methanesulfonyl-phenyl)-piperidine hydrochloride (20 mg), glacial acetic acid (4.4 mg) and 2-butanone (5.1 mg) were mixed in 1,2-dichloroethane (5 mL). Sodium triacetoxyborohydride (23.5 mg) was added to the solution and the reaction mixture was stirred at room temperature under a nitrogen atmosphere for 5 h (G.L.C. analysis indicated a complete reaction). The reaction was quenched with saturated aqueous NaHCO3 and the product was extracted with CH2Cl2. The combined organic phases were dried (MgSO4), filtered, and the solvent was evaporated to afford 1-sec-butyl-4-(3-methanesulfonyl-phenyl)-piperidine as an oily residue. The product was chromatographed on a silica column with CH2Cl2:MeOH (9:1 (v/v)) as eluent. Collection of the fractions containing pure product and evaporation of the solvent afforded pure amine (15 mg, 71%); MS m/z (relative intensity, 70 eV) 295 (M+, 1), 280 (7), 266 (bp), 187 (4), 129 (4).

Workup

  1. customa complete reaction)
  2. customThe reaction was quenched with saturated aqueous NaHCO3
  3. extractionthe product was extracted with CH2Cl2
  4. dry with materialThe combined organic phases were dried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-557ddb30738b4b74a1ed7c20d0152b41
Source dataset
uspto-grants-2016_08
Patent number
USRE046117E1

Reaction notes

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