Diisopropylethylamine → (4-Hydroxy-[1,4']bipiperidinyl-1'-yl)-(3-methanesulfonyl-phenyl)-methanone

HRID 1060821Notes

Reaction equation

HRID 1060821 reaction equation
C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[CH3:25][S:26]([C:29]1[CH:30]=[C:31]([CH:35]=[CH:36][CH:37]=1)[C:32]([OH:34])=O)(=[O:28])=[O:27].Cl.Cl.[N:40]1([CH:47]2[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]2)[CH2:45][CH2:44][CH:43]([OH:46])[CH2:42][CH2:41]1.CCN(C(C)C)C(C)C>ClCCl.CO>[OH:46][CH:43]1[CH2:42][CH2:41][N:40]([CH:47]2[CH2:52][CH2:51][N:50]([C:32]([C:31]3[CH:35]=[CH:36][CH:37]=[C:29]([S:26]([CH3:25])(=[O:27])=[O:28])[CH:30]=3)=[O:34])[CH2:49][CH2:48]2)[CH2:45][CH2:44]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2203803-Methanesulfonylbenzoic acidHCID 2733179PyBroPHCID 223975061-(4-Piperidinyl)-4-piperidinol dihydrochloride

Product 1

HCID 22397427(4-Hydroxy-[1,4']bipiperidinyl-1'-yl)-(3-methanesulfonyl-phenyl)-methanoneYield 87.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

PyBrOP™ (25.3 g) was added to a stirred solution of 3-methanesulphonyl benzoic acid (10 g), [1,4′]bipiperidinyl-4-ol dihydrochloride (13 g, see Method D) and Hunig's base (34 ml) in dichloromethane (500 ml). The resulting mixture was stirred at RT overnight, then washed with saturated NaHCO3 solution (300 ml) followed by saturated brine (300 ml). The organic layer was dried (MgSO4) and evaporated to leave an oily residue. Column chromatography (silica, 20% methanol in DCM) gave the product as a white solid (16 g; MS: APCI+(M+H) 367).

Workup

  1. washwashed with saturated NaHCO3 solution (300 ml)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customevaporated
  4. customto leave an oily residue

Sources & evidence

ORD record
ord-c85911b2e81049daae18f4798490badd
Source dataset
uspto-grants-2003_02
Patent number
US06525070B2

Reaction notes

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