HCID 13039253, compound → HCID 70481907, compound

HRID 851044Notes

Reaction equation

HRID 851044 reaction equation
C([O:8][C:9]1[CH:28]=[CH:27][C:12]([O:13][C@@H:14]2[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][C@H:15]2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.[H][H]>C(O)C.O1CCCC1.[Pd]>[OH:8][C:9]1[CH:28]=[CH:27][C:12]([O:13][C@@H:14]2[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][C@H:15]2[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[CH:11][CH:10]=1

Participants

6

Reactant 2

HCID 13039253HCID 13039253, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 70481907HCID 70481907, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 8.59 g of trans-4-(4-benzyloxyphenoxy)-1-methyl-3-phenylpiperidine in a mixture of 100 ml of absolute ethanol and 50 ml of tetrahydrofuran is hydrogenated overnight over 5% palladium-on-carbon at room temperature under 45 pounds per square inch of hydrogen. The catalyst is filtered and washed with ethanol and ether. The filtrate is concentrated in vacuo to a nearly colorless, partially solidified foam. Trituration of the foam with ether followed by recrystallization from 270 ml of chloroform gives product as a colorless solid, mps 169.5° C., 170°-172° C.

Workup

  1. filtrationThe catalyst is filtered
  2. washwashed with ethanol and ether
  3. concentrationThe filtrate is concentrated in vacuo to a nearly colorless, partially solidified foam
  4. customTrituration of the foam with ether followed by recrystallization from 270 ml of chloroform
  5. customgives product as a colorless solid, mps 169.5° C., 170°-172° C.

Sources & evidence

ORD record
ord-a9beea724f0448a5ae7d7214c70a2758
Source dataset
uspto-grants-1983_05
Patent number
US04382141

Reaction notes

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