Water → HCID 18919886, compound

HRID 1291068Notes

Reaction equation

HRID 1291068 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[NH2:17][C:18]1[CH:27]=[CH:26][C:21]([C:22](OC)=[O:23])=[CH:20][CH:19]=1.O>C1(C)C=CC=CC=1>[NH2:17][C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:14][CH:11]2[CH2:12][CH2:13][N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:9][CH2:10]2)=[O:23])=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 12082Methyl 4-aminobenzoateHCID 24758Sodium hydrideHCID 784611-Benzylpiperidin-4-ol

Product 1

HCID 18919886HCID 18919886, compoundYield 38.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

3.98 g (0.02 mol) of 1-benzyl-4-hydroxy-piperidine in 70 ml of toluene were treated with 0.624 g of NaH (50%) and heated at reflux for 1 1/2 hr. while gassing with argon. Subsequently, 3.32 g (0.022 mol) of methyl 4-amino-benzoate dissolved in 80 ml of toluene were added dropwise over 1/2 hr. and the mixture was heated at reflux for a further 2 hrs. The suspension obtained was added to 400 mi of water and the mixture was stirred. The precipitate was filtered off under suction and washed with toluene and hexane. The organic phase of the filtrate was separated, washed three times with water, dried over MgSO4 and evaporated and the residue was combined with the filter material. Chromatography was carried out over silica gel with chloroform as the eluent and recrystallization was carried out from ethyl acetate/hexane. 2.4 g (38.7%) of 1-benzyl-piperidin-4-yl 4-amino-benzoate were obtained as colorless crystals; m.p. 119°-120° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 1/2 hr
  3. additionwere added dropwise over 1/2 hr
  4. temperatureand the mixture was heated
  5. temperatureat reflux for a further 2 hrs
  6. customThe suspension obtained
  7. filtrationThe precipitate was filtered off under suction
  8. washwashed with toluene and hexane
  9. customThe organic phase of the filtrate was separated
  10. washwashed three times with water
  11. dry with materialdried over MgSO4
  12. customevaporated
  13. customChromatography was carried out over silica gel with chloroform as the eluent and recrystallization

Sources & evidence

ORD record
ord-5727219b13d842a289e2aee4dc9e923a
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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