HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1957045Generated: November 1, 2026
Water → 1-(Benzyloxycarbonyl)-4-phenylpiperidine-4-carboxylic acid
https://huagongshe.com/reaction/1957045
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Benzyl chloroformate | HCID 10387 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | 4-Piperidinecarboxylic acid, 4-phenyl-, 4-methylbenzenesulfonate (1:1) | HCID 2723657 | — |
| Solvent | Acetone | HCID 180 | — |
| Product | 1-(Benzyloxycarbonyl)-4-phenylpiperidine-4-carboxylic acid | HCID 22741798 | 90.3% |
Reaction Steps
A mixture of 37.7 g of 4-carboxy-4-phenylpiperidine p-toluenesulfonate, 53.3 g of 30% aqueous NaOH solution and 250 ml of water is cooled to 5° C. A solution of 18 g of benzyl chloroformate in 60 ml of acetone is added rapidly at 5° C. and the reaction mixture is stirred overnight while the temperature is allowed to rise to RT. It is washed twice with ether and, after decantation, the aqueous phase is acidified to pH 1 by the addition of concentrated HCl and then 2N HCl. The precipitate formed is wrung, dried, taken up with ether and wrung again to give 30.6 g of the expected product. M.p.=142°-144° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05780466 |
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| Source dataset | uspto-grants-1998_07 |
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| ORD ID | ord-7acb641f36364716929eecb29d236c94 |
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| Source note | uspto-grants-1998_07 |
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