Chloroform → Benzyl 4-(3-ethoxy-3-oxopropyl)piperidine-1-carboxylate

HRID 1195661Notes

Reaction equation

HRID 1195661 reaction equation
[C:1]1([CH2:7][O:8][C:9](Cl)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:12]1[CH2:17][CH2:16][CH:15]([CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:14][CH2:13]1.C(=O)([O-])[O-].[Na+].[Na+].ClC(Cl)Cl>O>[C:1]1([CH2:7][O:8][C:9]([N:12]2[CH2:17][CH2:16][CH:15]([CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:14][CH2:13]2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 10012639Ethyl 3-piperidin-4-ylpropanoate

Product 1

HCID 14989191Benzyl 4-(3-ethoxy-3-oxopropyl)piperidine-1-carboxylateYield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 54 parts of (phenylmethyl)carbonochloridate, 60 parts of ethyl 4-piperidinepropanoate, 31.8 parts of sodium carbonate and 600 parts of trichloromethane was stirred overnight at room temperature. Water was added and the layers were separated. The organic layer was dried, filtered and evaporated. The residue was purified by filtration over silica gel using a mixture of trichloromethane and methanol (99:1 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 71 parts (74%) of ethyl 1-(phenylmethoxycarbonyl)-4-piperidinepropanoate as a residue (interm. 1).

Workup

  1. customthe layers were separated
  2. customThe organic layer was dried
  3. filtrationfiltered
  4. customevaporated
  5. filtrationThe residue was purified by filtration over silica gel using
  6. additiona mixture of trichloromethane and methanol (99:1 by volume) as eluent
  7. customThe pure fractions were collected
  8. customthe eluent was evaporated

Sources & evidence

ORD record
ord-08ff2416e8c942d3a0575bc504629310
Source dataset
uspto-grants-1992_05
Patent number
US05112825

Reaction notes

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