Dimethylformamide → Methyl 2-(benzyloxy)-5-(piperidin-1-yl)benzoate

HRID 454497Notes

Reaction equation

HRID 454497 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]Br.CN(C)C=O.[NH2:19][C:20]1[CH:21]=[CH:22][C:23]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[C:24]([CH:29]=1)[C:25]([O:27][CH3:28])=[O:26]>C(OCC)(=O)C.O>[CH2:31]([O:30][C:23]1[CH:22]=[CH:21][C:20]([N:19]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)=[CH:29][C:24]=1[C:25]([O:27][CH3:28])=[O:26])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 81001,5-DibromopentaneHCID 11430Potassium CarbonateHCID 23019162Methyl 5-amino-2-(benzyloxy)benzoate

Product 1

HCID 66990377Methyl 2-(benzyloxy)-5-(piperidin-1-yl)benzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

Potassium carbonate (5.1 g) and 1,5-dibromopentane (2.5 mL) were sequentially added to an N,N-dimethylformamide (23 mL) solution of methyl 5-amino-2-(benzyloxy)benzoate (4.6 g), followed by stirring at 50 to 55° C. for 1 hour, at 55 to 60° C. for 1 hour, at 70° C. for 1 hour and 30 minutes, and then at 75 to 80° C. for 1 hour and 30 minutes. The reaction mixture was cooled to room temperature, and then water and ethyl acetate were added thereto. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: 95-65% hexane/ethyl acetate] to obtain 4.3 g of methyl 2-(benzyloxy)-5-(piperidin-1-yl)benzoate as a light yellow oily substance.

Workup

  1. waitat 75 to 80° C. for 1 hour
  2. custom30 minutes
  3. temperatureThe reaction mixture was cooled to room temperature
  4. customThe organic layer was separated
  5. washwashed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: 95-65% hexane/ethyl acetate]

Sources & evidence

ORD record
ord-d97f99c18f2d4c69acbacdede2703939
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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