Hydrochloric Acid → 4-(4-Bromophenyl)-1-(methanesulphonyl)piperidin-4-ol

HRID 222571Notes

Reaction equation

HRID 222571 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[Br:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2([OH:19])[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[CH:9][CH:8]=1.C(N(CC)CC)C.Cl>O1CCCC1>[Br:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2([OH:19])[CH2:14][CH2:15][N:16]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:17][CH2:18]2)=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 939114-(4-Bromophenyl)-4-hydroxypiperidine

Product 1

HCID 187232054-(4-Bromophenyl)-1-(methanesulphonyl)piperidin-4-olYield 93.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

Methanesulfonyl chloride (21.91 g, 14.81 mL, 191.30 mmol) is added slowly (10 min) to a solution of 4-(4-bromophenyl)-4-piperidinol (50.00 g, 191.30 mmol) and triethylamine (29.04 g, 40.00 mL, 286.95 mmol) in tetrahydrofuran (575 mL) at 23° C. (internal temperature) under nitrogen atmosphere. The mixture is stirred at 23° C. for 30 min. 500 mL of 1 M aq hydrochloric acid are added and the mixture is stirred for 10 min. The mixture is extracted with ethyl acetate (2×500 mL) the organic layers are combined, dried over anhydrous sodium sulfate, filtered and the solvent is removed to obtain 60.0 g of the title compound as a white solid. MS m/e (79Br/81Br) 333, 335 (M+1).

Workup

  1. stirringthe mixture is stirred for 10 min
  2. extractionThe mixture is extracted with ethyl acetate (2×500 mL) the organic layers
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customthe solvent is removed

Sources & evidence

ORD record
ord-4101cdef24d94e88b26111bce781f050
Source dataset
uspto-grants-2012_06
Patent number
US08207344B2

Reaction notes

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