1,4'-Bipiperidine → HCID 68543804, compound

HRID 1446016Notes

Reaction equation

HRID 1446016 reaction equation
[CH3:1][C:2]([O:4][C@H:5]1[C:14]2[C@@:15]3([CH3:30])[C@@H:26]([CH2:27][O:28][CH3:29])[O:25][C:23](=[O:24])[C:17]4=[CH:18][O:19][C:20]([C:21](=[O:22])[C:13]=2[C@@H:8]2[CH2:9][CH2:10][C@H:11]([OH:12])[C@@:7]2([CH3:31])[CH2:6]1)=[C:16]34)=[O:3].[N:32]1([CH:38]2[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]2)[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1>C(Cl)Cl>[N:32]1([CH:38]2[CH2:43][CH2:42][N:41]([CH:18]=[C:17]3[C:16]4[C:15]([CH3:30])([C:14]5[CH:5]([O:4][C:2](=[O:3])[CH3:1])[CH2:6][C:7]6([CH3:31])[CH:8]([C:13]=5[C:21](=[O:22])[C:20]=4[OH:19])[CH2:9][CH2:10][CH:11]6[OH:12])[CH:26]([CH2:27][O:28][CH3:29])[O:25][C:23]3=[O:24])[CH2:40][CH2:39]2)[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1

Participants

4

Reactant 2

HCID 786071,4'-BipiperidineHCID 986734017beta-Hydroxy wortmannin

Product 1

HCID 68543804HCID 68543804, compoundYield 72.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

17-Hydroxywortmannin (30 mg, 0.069 mmol) is dissolved in 2 ml methylene chloride and stirred at room temperature under nitrogen atmosphere as 4-piperidinopiperidine (0.069 mmol, 11.6 mg) is added. The reaction solution turns orange immediately. After 30 min, the solvent is evaporated and the solid is recrystallized from ethyl acetate/hexane (2:1). After filtration, the solid is washed with hexane and dried under vacuum to yield about 30 mg the title compound as an orange powder. UV λmax (CH3CN/H2O): 250 nm, 320 nm, 397 nm; Positive ESI-MS: m/z 599 [M+H]+.

Workup

  1. additionis added
  2. customthe solvent is evaporated
  3. customthe solid is recrystallized from ethyl acetate/hexane (2:1)
  4. filtrationAfter filtration
  5. washthe solid is washed with hexane
  6. customdried under vacuum

Sources & evidence

ORD record
ord-b72960f767744966ac64b3aa699ba08f
Source dataset
uspto-grants-2010_02
Patent number
US07666901B2

Reaction notes

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