Methanol → HCID 86670972, compound

HRID 515341Notes

Reaction equation

HRID 515341 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:18])[CH3:17])=[CH:11][CH:10]=2)=[O:8])[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]([OH:42])([C:38]([F:41])([F:40])[F:39])[C:34]([F:37])([F:36])[F:35])=[CH:29][CH:28]=1.CO>CN1CCCC1=O>[F:35][C:34]([F:36])([F:37])[C:33]([C:30]1[CH:31]=[CH:32][C:27]([CH2:26][N:1]2[CH2:2][CH2:3][CH:4]([C:7]([C:9]3[CH:10]=[CH:11][C:12]([NH:15][C:16](=[O:18])[CH3:17])=[CH:13][CH:14]=3)=[O:8])[CH2:5][CH2:6]2)=[CH:28][CH:29]=1)([OH:42])[C:38]([F:39])([F:41])[F:40]

Participants

6

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 15680074N-[4-(Piperidine-4-carbonyl)phenyl]acetamideHCID 235273962-[4-(Bromomethyl)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-ol

Product 1

HCID 86670972HCID 86670972, compoundYield 78.7%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a stirred mixture of N-(4-(piperidine-4-carbonyl)phenyl)acetamide (3.82 mmol, 0.94 g) and potassium carbonate (11.45 mmol, 1.582 g) in N-methyl-2-pyrrolidinone (5 mL) was added 2-(4-(bromomethyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (3.82 mmol, 1.286 g). The reaction was stirred at room temperature over the weekend. Methanol (30 mL) was added and the reaction was filtered. The filtrate was purified by strong cation exchange column chromatography to afford the title compound (1.51 g).

Workup

  1. filtrationthe reaction was filtered
  2. customThe filtrate was purified by strong cation exchange column chromatography

Sources & evidence

ORD record
ord-816dc61ada274b2d88e0b4b822d3c7af
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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