Dimethylformamide → HCID 70873664, compound

HRID 2172220Notes

Reaction equation

HRID 2172220 reaction equation
[OH:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.[F:33][C:34]([F:44])([F:43])[C:35]1[CH:42]=[CH:41][C:38]([CH2:39]Br)=[CH:37][CH:36]=1>O>[C:16]([O:15][C:13]([N:10]1[CH2:9][CH2:8][CH:7]([CH2:6][C:5]2[CH:20]=[CH:21][C:2]([O:1][CH2:39][C:38]3[CH:37]=[CH:36][C:35]([C:34]([F:33])([F:43])[F:44])=[CH:42][CH:41]=3)=[CH:3][CH:4]=2)[CH2:12][CH2:11]1)=[O:14])([CH3:17])([CH3:18])[CH3:19]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 68225397tert-Butyl 4-(4-hydroxybenzyl)piperidine-1-carboxylate

Product 1

HCID 70873664HCID 70873664, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

tert-Butyl 4-(4-hydroxybenzyl)piperidine-1-carboxylate (1.78 g, 6.1 mmol), potassium carbonate (1.27 g, 9.2 mmol), N,N-dimethylformamide (18 ml) and 4-(trifluoromethyl)benzylbromide (1.75 g, 7.3 mmol) were mixed and stirred at room temperature overnight. The reaction mixture was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate, and then concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→60:40) to afford the title compound as a colorless powder (2.64 g, 96%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→60:40)

Sources & evidence

ORD record
ord-b83bcfe0e3384e58b9f5b787584cd15f
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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