HCID 12788407, compound → HCID 70513832, compound

HRID 851014Notes

Reaction equation

HRID 851014 reaction equation
[ClH:1].[N+](C1C=CC(O[C@H:10]2[CH2:15][CH2:14][NH:13][CH2:12][C@H:11]2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=CC=1)([O-])=O.[H][H].Cl.[NH2:27][C:28]1[CH:46]=[CH:45][C:31]([O:32][C@H]2CCNC[C@H]2C2C=CC=CC=2)=[CH:30][CH:29]=1>C(O)C.O.[Pd]>[ClH:1].[NH2:27][C:28]1[CH:46]=[CH:45][C:31]([O:32][N:13]2[CH2:14][CH2:15][CH2:10][CH:11]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:12]2)=[CH:30][CH:29]=1

Participants

7

Reactant 3

HCID 12788407HCID 12788407, compoundHCID 70513794HCID 70513794, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 70513832HCID 70513832, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 4.1 g of cis-4-(4-nitrophenoxy)-3-phenylpiperidine hydrochloride, of Example 10, in a mixture of 125 ml of 95% aqueous ethanol and 5 ml of water is hydrogenated at 45 psi of hydrogen at room temperature over 0.41 g of 10% palladium on carbon catalyst. After 18 hours the catalyst is filtered off and the filtrate concentrated in vacuo. The resulting solid is triturated with ether and filtered to afford a nearly white salt, m.p. s 221°, 223.5°-225.5° C., of cis-4-(4-aminophenoxy)-3-phenylpiperidine hydrochloride.

Workup

  1. filtrationAfter 18 hours the catalyst is filtered off
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe resulting solid is triturated with ether
  4. filtrationfiltered
  5. customto afford a nearly white salt
  6. customs 221°, 223.5°-225.5° C.

Sources & evidence

ORD record
ord-dd76d038cfa74b0594486c59d2e8c6a3
Source dataset
uspto-grants-1983_05
Patent number
US04382141

Reaction notes

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