Potassium Carbonate → Ethyl 4-(diphenylmethoxy)piperidine carboxylate

HRID 354968

Reaction equation

HRID 354968 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][CH:9]([OH:12])[CH2:8][CH2:7]1)=[O:5])[CH3:2].Br[CH:14]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>O>[C:15]1([CH:14]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[O:12][CH:9]2[CH2:8][CH2:7][N:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:11][CH2:10]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 96394Ethyl 4-hydroxypiperidine-1-carboxylateHCID 236603Bromodiphenylmethane

Product 1

HCID 10020094Ethyl 4-(diphenylmethoxy)piperidine carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 17.3 parts of 1-(ethoxycarbonyl)-4-hydroxypiperidine, 24.7 parts of bromodiphenylmethane and 7 parts of potassium carbonate is stirred and heated in an oil-bath for 3 hours at 140° C. The reaction mixture is cooled, water is added and the product is extracted with methylbenzene. The extract is washed a few times with water, dried, filtered and evaporated. The oily residue is distilled, yielding ethyl 4-(diphenylmethoxy)-1-piperidinecarboxylate; bp. 150° C. at 0.4 mm. pressure.

Workup

  1. temperatureThe reaction mixture is cooled
  2. extractionthe product is extracted with methylbenzene
  3. washThe extract is washed a few times with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. distillationThe oily residue is distilled

Sources & evidence

ORD record
ord-276822bab8634971bcbaf70aa53751a4
Source dataset
uspto-grants-1983_03
Patent number
US04377578

Linked notes

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