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

HRID 1293540Notes

Reaction equation

HRID 1293540 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-9985c44519074298b6398a4efd53a7f5
Source dataset
uspto-grants-2007_07
Patent number
US07238811B2

Reaction notes

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