Triethylamine → 4-(4-Bromophenyl)-1-(methanesulphonyl)piperidin-4-ol

HRID 41703Notes

Reaction equation

HRID 41703 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:14])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:14])[CH2:9][CH2:10][N:11]([S:23]([CH3:22])(=[O:25])=[O:24])[CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

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

Product 1

HCID 187232054-(4-Bromophenyl)-1-(methanesulphonyl)piperidin-4-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1 g of 4-(4-bromophenyl)piperidin-4-ol is placed in 20 ml of dichloromethane. 0.65 ml of triethylamine and then 0.33 ml of methanesulphonyl chloride are added. The reaction mixture is stirred at ambient temperature for 2 h. It is washed with water and then with a saturated aqueous sodium chloride solution. The organic phase is dried over sodium sulphate and then evaporated under reduced pressure. The crude product obtained is chromatographed on silica gel, elution being carried out with a dichloromethane/methanol (99/1) solvent mixture. 1.1 g of 4-(4-bromophenyl)-1-(methanesulphonyl)piperidin-4-ol are obtained.

Workup

  1. washIt is washed with water
  2. dry with materialThe organic phase is dried over sodium sulphate
  3. customevaporated under reduced pressure
  4. customThe crude product obtained
  5. customis chromatographed on silica gel, elution

Sources & evidence

ORD record
ord-912b160d0d294e57b5d2e395040ec0ab
Source dataset
uspto-grants-2013_09
Patent number
US08530657B2

Reaction notes

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